SCIENTIFIC ABSTRACT FODOR, E. - FODOR, G.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R000413330012-4
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: June 13, 2000
• Sequence Number: 12
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

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FODOR, E.i MARAZAN, N.; MERC&A, V.; OLARIIJ, A.
Nitrogen influence on the reaction of isotopic exchange between
hydrogen and watery vapors. Studii care fia 14 no.1:7-23 163.
1. Institutul de fizica atomica, Sectia. Cluj,. Universitatea
nBabes-4yain Facultatea de fizica, Cluj.

MERCFA, V.; FODOR, E.; GRECU, V.
Separation in a column with steam distillation depending
on the medium concentration of the mixture. Studia Univ
B-B S. Math-Phys 7 no.1:137-147 162.
Q

UNGUMIA1111J) C.; FODOR, E.
Spectral analysis of poor alloyed steels. Rev chimie I-Lin petr
14 no.8:467-469 Ag 163.
1. Institutul do fizica atomica, Sectia Cluj (for Ungureanu).
2. "Industria sirmeill- Cimpia Turzii, laboratorul central (for
Fodor).

Fr Dc R, -- FZR&,IC
Balla Antal; elete es muszaki munkassal-a (1739-1815). Budapest.
Tankonyvklado (1-953) 59 P. (Budapeati Muszaki E3,yetem Kozponti
Konyvtara. Muszaki tudomanytorteneti kladvanyok, 2. szam) (Antal
Balla; his life and technical actIvitles (1739-1915). English and
Russian sumaries. maps) GtYy Not in DLC
SOURCE: Monthly list of East European Accessions, (ESAL), W,
Vol. 5. No- 3, March, 1956

(To be Cont,d)f" P. Euda a,--, r.1,L,
2_25, (FCLEfTIF*.~I."':I
Budaoest, Hungary)
"C: Ionthly List (If Fast Eurcnean Accessicns
Y'arch 1?55, Uncl.
r
4, 1954,
J,C c1

FOD,,~,R, FERE-NC
Balla Antal elete es muszaki murflassaga (17-39-1815). Budaf)est, Tankanyvkiado
(1953) P. 59. (Budapest. Muszaki Egyetem. Kozponti Konyvtara. 11~iszaki
tudomanytorteneti kiadvanyok, 2. sz.) (Antal Balla's life and technical activities
1739-1-815) Enrlish and hus-ian summaries. maps. b1bl., facsL-n.
Cty IU
SO: Monthly List of East European Accessions (E---.tL) Le, Vol. 6, no. 6, June 1957. Uncl.

C,
1/0 7. Alliat Hallit, (Wagariatl Ilystraulle tugluccr Of (lie
18111 century. 1'. F is it is r.
Vo I,3, 1055, 374
Autong tile Ity(tratille ellgilwers; of his time Aida[
halhi (17 wa.-i title of lite most prOtilinvat
representatives tof ljf,~i profC"foll. At it Ifille wht'll tile
elvillms training of coginix.rs was pravikally nua-
ex6teut In Vurofse Anial lialla had It -icleatific eruditi.st,
which surpa-.4std by far-thatol"It6conWill lorarles. In
the elghtle!i of the (BUt Celitury 1w Nva% one o Itutigary's
most excellent and best vdkicated tteluilchus with it
Mile intellectual horlion who at Uic same flint: wam it
lll(*t exact and IlIgIlly hkutVil CUrtograplicr ti.,t well.
Several "cellent inaps am) &.sigum for a sitalt- bridq
WIMMilig PtSt luld H utits WVTU 1160 fUM111 nlill,iig III$
ra IILS WOtk Oil tlawry (I( provvd
Mit Al otastuntillig pily.410-it. 104
tie it IUIL Wds 111"o oil 11 high leveL Ile wrole
urchitt-ology. theory of junsic Laud history, .4 CI v
wark-A however concvriml hydratilks. Its, WaS the firA
if) gleAgn a Callus Comlecting the Dilistil- awl'til%: 'j*iSI
-dyers for wittdi rawtl with renlArkalliv title
-hgjtjpi_-tt j., _.__
tCC1 'I- i_ -v it inap includitig iia-11qtdeaAtu-*---
aud bydrogralAdval explamillimi.-I V
and Milo's ti;; an-d I-, in imim teat lost.

BLUMT. Ferenc, dr..; YODOR, Yerenc. dr.
Postoperative results in the therapy of chronic purulent
infootion of the middle ear. Ful orr gegeg3rogy. no.4:112-116 Nov. 53
1. Baja Varosi Tanacs, Korhaza ful-, Orr-. Gogeosztalyanak (foorvos:
Banhidy Fereno dr.) koslevenys.
(OTITIS MIDIA. surgery
radical. results in chronic)
J:1

MDOR, Ferenc, dr.
About the cleanness campaign. NOVegeezvegugY 37 no.4.#109-110
Apr 56.
1. Koslameny a Hajdii-Bihar meg7el kozegesseegugyi-jarvanyiWi
allomaerol (igaigato-foorvoo: Fodor, Ferenc dr.)
(PUBLIC HEALTH
In Hungary, campaign for promotion of hygiene in
public Institutions, schools & industry. standards (Run))

MNHDY. Yerenc. dr..; PCOOR, Foreac, dr.
Tuberculosis of the tonsils in pulmnary tuberculosis. Orv. hatil.
97 no.4:100-103 22 Jan 56.
1. A Baja Varosi Tanacs Xorhaza (igesgato- Barg Ito dr. imadidatus)
Ful-orr-gege Osztalyanak (foorwoo: Banhidy Ferene dr.) kozlemenyo.
(TCOSUB. die.
tuberc. with puln. tuberc., tonsillectoaW & pathol.
(Run))
(TUMOULOSIS, PUINCKARY, compl.
tubera. of tonsils, tonsillectomy & pathol. (Hhn))

" ^
~_ IjC_ V\ "tQ_
F
KOTAY, Pal, Dr.; GREPALY, Andras, Dr.; BALOGH, Brno; FODOR, Ferene
Problems of renal tuberculosis in children and in puberty. Xagy,
sebesset 10 no.2-3:183-188 Apr-Jane 57-
1. Tirgu-Nuros--Naroevanearholy (Rumnia)
(TUBMUIDSIS, RINA4 in inf. & child
in child. & in puberty (Hun))

FODOR, 7erente, [Yodor, Ferenc] (Yongerskaya Narodnava Respublika)
Public health organization in Hajdvo-Bihar region. Sov.zdrave
17 no,los47-51 0 158 11311)
(PMLIO HEAIM,
in Hungary (Rue))
N "r
N

1FODOR, Forenc, dr.
Medical ethics and basic problems of medical legislation. Ory.
hetil. 100 no-50:1800-1803 D '59.
(WHICS, KKDICAL)
(LIGISIATION, KIDICAL)

GYJMYAY,Z.,Assl8t- Prof.; -FODOR F. ANTALM,A.; STROMPEL,.E.
Contributions to the morphologyof the diabetes insipidue syndrome.
Rumanian M. Rev. 4 no.1:3-6 Ja-* 160.
(DIARIM INSIPIMUS etiol.)
(PITUITARY GLWD die.)

MONOKIt St., dr.; HORVATH, Eva, dr.; WIENER, 1?r,, cir.; FODOR, 1?r,,, dr.
Heart diseases in collagen diseases. Yled. inter., Buc= 13 no.2:
195-199 F 161.
1. Luorare efectuata in Clinics. a II-a modicala, Catedm de anstomis
patologica si Catedra de biologie, Tg. Mures.
COLLAGEN DISEASES emplicationa)
ART DISEASES atio3.ogy)
M

FODOR, Ferenc, dr.; EGMIj Laszlo, dr.
Morbidity structure chamgeo observed by district physicians in a
central area of Budapest. Nepegeassegugy 42 no.9:268-271 S 161.
1. Kozlemeny a Budapeeft Orvostudomanyi Egyetem Kozegeszsegtani Intezete-
bol (tansselmezeto profeBszor: Melly Tozsef dr. egyetemi tanar) es a
fovarosi tanace Trefort utcai rendelointezatebol)
(MORBIDITr statist)

,FODOR, Ferenc,dr.; SZAKKA 1, Antal, dr.
Sow epidemiological data on tuberculosis obtained during bontact
.preventive exudnationao Repopossegugy'43 no.ltl2-14 Ja 162.
(TMMULOSIS spidesiol)

Morbidity in various regions of Budapest according to data,- on the
turnover of patienta. Nepegansogugy 43 no.6;166-171 Je 162.
1. Kozlemeny a Budapesti Orvostudomanyi --gyetem Kozegeszsegtani
Intezetebol (ianszekvezetos Molly Jozsof dr. egyetemi tana
(MORBIDITY)
44
-on

FODOR, Ferenc, dr.; MADAI, Lajos, dr.
Emergency hospitalizations in Budapest, with ppecial reference to
internal medicine wards. Repegeszsegugy 43 no.11:337-344 V 162.
. . 1. 1
1. Kozlemenr a Budapesti Orvostudomanyi Egyetem Kozegeszsegtani Intezetebol
es a Fovarosi Tanace VB Egeszsegugyi Osztalyarol.
(HOSPITALIZATION) (EMERGRICIES) (INTERNAL MEDICINE)

FO ~4,~__teren~,Jr.; SZAKKAY., Antal., dr..
Epidemiological significance of a pathological form of tuberculosis
based on contact morbidity withis the family. Tuberkulozis 16 no.l:
7-12 A 163.
1. A Budapesti. Orvostudomanyi Egyetem, Kozegeszoogtani Intezete es
a Fovarosi Kozponti Tbe-Gondoiointezet koalemenyo.
(TUB M-CULOSIIS)

FODOR, -FaroD,t -encl. d,)ktor; MAMI, layosh, [mada:i, L-AJOS;
. -,I.-.[Fodor, Fai
doktor (RTa_~e`sh__t_)_'
Hospitalization of therapeutic patients for emergency causes
in Budapest. Sov. zdrav. 22 no.7t68-71 163 .N~ 16:10 1,

MD!~t, Ferpn.c,,dr.; HADAI, lajos, dr.
Emergency admissions to surgical departments of Budapest hos-
pitals. Nepegeszoegugy 1+5 no.ltll8-120 Ap'61+
1. Kozlemeny a Wdapesti Or7ostudomanyi Egyetem Kozegeszseg~
tani Intezetebol es a Fovarosi Tanacs VB Egeszaegugyi Osz-
talyarol.

FODOR C1. 'Szeged)
p k
Equivalence of a problem of set theory to a bypotheiis concerning
the powers of cardinal numbers. Acta math Szeged 24 no.1/2i152-
156 163.
1. Submitted July 15, 1962.

FODDRI G. (Szegod)
` w. .
application of the theory of regressive functions. Acts,
math Szeged 24 no.3As255-257 163.
1. Submitted April 18, 1963.
1

Obt!t 1 ft. ng 19 Fo w! thout-, carr Io r. F~nv ch!!O e Rou!n. 9 10: 0
in ill dor-,Y, "jlc ar.,
C)i -trolic, Aly'li(m or the 'u

AT R
PE',Z-,")DTCAIS: ftRTA FPe4p
4aA Vol ")i ITO 7/- Jill, /Au,. I
MAGYAR KE,11AI ;%01:10VIAT
Fodor, A rodified s3~rit'hesis of scopolamine nnrl -+s Hncp,,'-P+-r.
,I-,,ntl,ilv list nf E-st FIMOT)ean Accessions (EEPAT) Lr, Vol. ITO. 5)
Februarr U,nclass.

FODOR GABORNE VARGA, Eva
An account of my study trip to Bulgaria. Kem tud kozl MTA
20 no.1:83-88 163.
1. Magyar Tudomanyos Akademia Sztereokemiai Kutato Csopartja,
Budapest.

PARASCHIV, Virginia, ing.; FODOR, Georgeta, ing.
Tests on the measurement of pressures inside the road layers using
electric doses. Rev transport 10 no-4:158-162 Ap 163.
.1

TEODORESCU Dorina ing.; FODOR Georgeta, ing.
J, .9 . ~--. A--, -1-1-...-,-,- -.
Laboratory studies on the use of thermoelectric power station
ash for Rumanian road construction. Rev transport 10 no. 7:
311-316 il 16.3.

FODOR, Georpta, ing.; IIJRCU . Marius, ing.
Studies of bearing capacity on the DIN 14 14adias-
Sighisoara route* ~Rev transport 10 no. 81 359-365
Ag 163.

IONF.SCU, ALI-acandr.,, -ing.; FODOR, Gaorgeta,, ing.
4
~~ - -r
i ~11.; 1~1-
Study of the way In which the road systems ~n the central
control station of the Institute of Transports and Tele-
communications meet the requirements impoged by heavy traffic.
Rev transport 11 no.lOs452-461 0 164.

FODOR, Gabor
Some questions relating to socialist morality. Manka 14 no.4s22 Ap 164,
1. Contributor, ONevszava", Budapest.

IIIA"A
1, its ti~ei ism alwas SZ-
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; Atli9"l,
with (he it" wninswrop4nol like IV. to. IM
.00
*04 Now "lithesis of arylacirtit dwds and wilwastiew _isr fr(m, the dtUwtlYIAt%%I JlCttylantino deriv. wid

00 & dolvatos having a 6=11tk Offect. (;Al.w Pods".
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nte turthi"I -.
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(110 will. it, "11.4 Willi 1 11.0, 1", ~30,1'); boon-ITI-Tati7l,
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-Uyl- Slist 1-1141"1-6111 A lorthyl
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FUDOR, G. 1948
t (Res. Labs. Chinoin Chem. & Pharmaceut. Works Ltd. Uipest, Hungary.)
"Investigations Relating to the Synthesis of Patulin."
Jour. of the Chemical 5ociety 1948 (Sept.) pp. 1295-1299
Abst: Exc. Med. 11, Vol. U. No. 10. p. 1360

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'i sik and degrebtive studies In the isaqulatilins -460
00 CIA twice. fit. V. Bruckner,
4,Y9.41, I Kcivici, and
Kipis (UnIv. Sageti, HunlrAry). . to". Chrm~ Sor. .40
00 .4 70, cf. C.A. 40. 61.41 '.-Pfeiffer, es at.
00 (CA. $4, 23MI), obtained A ccunpd. from brjuilln for
which they suggested the structure 1.(2-hydrazy4-meth. -04
oo (1); at.
00 V, tempted syntheds of I led to a to which they Lj-
signed the struicture of the 7,FArixV1(0_ Isomer (11). 2,4.
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is I mud not Uvid the structure of the product from Ismilis Vo 0
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CA-M Phi"
A,M V
to HuSl6b lBff4xts "eve mmak to synibe-
In a Wimb for
Wapelliko "W Gyntholds was mmoll W The
MIN110-11cl, W. 146*, pripl.
tN)s and NOUAW, was tmrWarvmk
lIsMiNlICONIts to 176. Into 8-(ft.
d - ~,. 44 W. ( 1 4 r
W. IkI. socardims to dark sodd
d(IODMI, was Converted Into (PhcIil)*-
(U). bat pMd. (67.6ro ykid) by ~-
LHSCN In ea. sk. Fromm U mW CICIfi-
arm
M.
which showed
Imiatic 41)"Y'
a am SIT".
Isivin Finily

The neemerimis of pritpettylbowe" and of sHylben
Igoe d4dutivem, Arpid Kia, C!Jtkw F(xtqr. ittJ I
Molnir. Adis Vale. Swgid. CAwW"R'PAji~. 2. W-111
mom (in Engiib).-fise uitmvioiet ahsorption cufveq tA
allyl and Pfopeo I phenol% and their ethers sho"I thAt
tile inesonlefic Xct of the submtituents wa,, in all V ,
larger than their inductive effect The curve, W Niv!
Itentene defivs. carresixinded clowir In 111~ of tile
lifirni4i :still plirnnl ribers, slight iliffirlences being Glur
(,iot, it) the intioctive effect a tile atio chAin- 'riw c,
Imclilln ut the Avi chain could tie eph-erved wily in ilw
&~vndins PArt lit tile curves. The Wwwplion Iwclr,i fit
.111 propittlyl derim, i.e., "nni, anetlu*, iWiellgellol.
kohornottent-A. *M4frtk. isnottyristicin. and ioachwoet44.
revealed it r1aw rewrobtince to that of PhOVC11MV
rins indicates that the r-eltetrous od the prulicnirl
chain play an important part in the tnesornerisatt lit pri*
Penylbenune dermt 1%tvin FillAv

S Naturit 164, 917-11;
(lN9).-lnVr2tjgAtjUII.* tit thV AVYI klkt-4111011 IcJCtIt'I
X - 0 (c(. C.A. 43, 4=4b) were rmend.-d to
imucric alicyclic arnino 214:8. tit "tablijil mcm po'lumv,
When 2-lientamidocyclolictianolit tit. 1911' mid 171 ' %ter,
11 treated scpAmtely with a1c. IICI at rmon twisip.. Ilie Isw
IUAtctial rcartarigol mitte rapidly (by a bettor of tit or 1.)
1111141 WAS OI1IXidCFCd tit IW Cis; it X-7e 0-1--vt
Ill. =,q*. at.. do.-ght t,- 1~
174 * Inatirli.d. voll'idered tit tv ti.61t., X.Ave 4, I,villo% I
111111in.)cYclotirza"ol-licl (tram). In. 2K1'. 11--ti, lit'l
salts wrre rrArratigrd to Itic migimil aittideS by alk,,11.
At ltlo* the rates of rear-ratigruieut J the '21 ami,l- new
III.-Fir stralir alikir, Imit the 'amv p1'.110, '1~ 1. log, "I I`
I4ilithicil. The %tudi- are t-, 1~ oxtrii&4 i,- t1w mm-
Wrtirols. 11. 11, %'%'

The aptislask of
falmooArloulkiworbalrylk
it nin.. Sirg"), 1141"S ). -1.1d i"l"l 3114.. (/W#". el.
PO". S, I-M. ask lilrooKin litisli,fil .-The por"."Ay""known
tweluji. 111 o61 41) (.Alt* coal.
figurativas; 4% v1shelfritirl wan prclul. by the Ifirlting aminis
.k-. Ynth"i.. Ott irratinent with alkali. I dermthmylatnt
ramly. Puttylt"', mwh a, all est. lif Suillonot-l'i Itiollsory. alut,
Imctly derarboisyla(vil 1, Istin-Ing that Its lieuvitior differs
Irmist that tot the rumnatm I.( the isomeric I-sruducithelfritior
-fw-. 3.4 1111) ht.11, WC1110 Popf (11). ton III' 2W. won
IIAttained Ivy UP, gA% bill) TJ q. in
XI S, Iffif Ift""I'410 tot :15 M' And emlills; with lee tolitif
llor InCfr4W In tit Wan UN it.. healing son A OCAM Will 411
min.. jonimurs"S wilb stirring into 1% g. VaOAc in 1!1111 tell.
""Itt, evols, The Oily with PtioOll air till", dry-
ing the nivierrif en fused MallSO,, sitstj di*lg, jig njo#-Mpvo~ Fj
*a,, toretuf
fly Adding IN 9~ ether %osln, r4 IICI to Z~ S. It In It*) nil.
.try ether. thers, %1.)*IY at It', I I S. 11"bly-olmd. IIUON'O too
Xi "d At., cities. krepillg mernight in it teffigeratm, land
-A. Ald -- ~ t
ivill"Vills live .4%fill At "if,' I't V40to
(IV). tit. I 1~" '-4?* 1. %4' v-1.14it"I by hystrtsit"Ut.
I 11.1-ch4or"d in he
iliff.111.3 K. III in IL4) 10. ah,. E'1011 1%4-
umLil ols4livief I~l hrl. it) the lifl-Wil"t (11 "1 "1 4 11 X IICI III
At". F011t. filterials, eval,jr. III v,".0 At 'As*. IiA%VA%iiig the
midur in At". r%spg. AgAll. load thitilig Its 49 -101k`
4-affIr I" the aA. .4 IV. :! S C. IV Ar'.1, 'halsen
with full nil. NAIIII m4a I for !is A visitrut .4 It. licullAblell
with IICI. hAri%fA!k%vjub% A cuffrut 14 It, lirfilloorifell with
it, I ll. 1417P I'll cha 4 ~ tAt-itteritt.,11I.AndfiltormL The
1144"Ith-1 wag Ia,.vivjC that dwarbovitylallm
Pl4re I When 3 9 IV wan lovelt'llYfrof In 'At 111111. N II(*t
tit A VIST11111 4 11 At -'01. I'll I Ill - ""Aff-I f%"'hV' An
jfl,l rise .,Ici, tot III,. I.mits, t tmatell sloth the deturl-strIA-
nof 11ofura-pig killney. ill the ri-e 4.1 the thrmthrri". obtairsord,
fly .4poic., 111) cOv hirinalit'n win IIbWfVr'j' wbrffts thor luls-
(Alil," fiblain"t fly 'Albin. 44 acittiliest coryllva" ciang"k. gv"-
es,.117 dv~vrl'vlftlt tatu'llethIr mts. ill COo. The tortichtet
fbMillrol Ill $)'I. A, 1.1 1'.11101ri, was 111101. 3,44110W.11.-
IIV1 "ith the r,yfk,o,, mvuctarr.
I,avin Hittite

(4
I "t 4' - 'N" - G"-4hq
LA =;","A t c
V h. .1 M 'Z ' L'-
;11; st vgs~rlolnuKf bX.1 7h Istry.
Ist4n MnAly

01/
C.. an of dittistmilisomeric 3 reidlitilty-11-hy-
&."Y loplinsilamines C.11I.W Ki", still
A,i,
firis Sit reke Witiv. Itillig:3 J. thf. Christ.
N
15. lMI91011; ri, C.A, 39, ~,W*V. tit the licelln. .4
3.4 li Its lWC.IIXIU( lit ~Clli Nli,),%I,- (11 hous Wt-
,ujiniot (11) tem l(CIIIN(l1CII,.%fl,I%lk- fk - 3.I-MtO-
tilt(`11,01C.11,1 - I(Clfif ill ICIff MIA"Me flIll -
kCll(f_lII)ClIs.Nly%Ie ilVI. A 1 (611. 111. '.5115% %1 Oll-
tAitiCtI. When I t- lisq-1. fimit It i,i., 3,4-%IvO(AMI.
J011WIll NIIAe)%It- (VI, " I 'lls). ol. 176" it oblailit'l.
Fla aml Ili Ali- 4-11111-11 it) 14- Accoril-
mg I-- Wr6h I C .1. 4 1.211QO. 11,1L.- Ifir colifigurAlioil
fle,-AUSC Ill Atilt V IUVV tit, -11te t OfiflKlir.1114KI AOY 01-olite
us it 111w( olTur either ill (it'. coilvvtmott of Ill into IV or
,luting thli IcAt%tVLlfiw 4-f V ]Ievailw rt-Acrtylatiolt tit
IV AKAJO, fill VILMKV ill 4-011figUrAlittlt C-Arl like
plArr duritic the driertylatimt, Atilt IV cowt kwe the clots-
figurAlitua of V1 1"tp prove 111.11 tit the ifearetyLitim of V
A W.Shir I% its Vt-f%ifNl i, 11-V
1, villfieitrif by a inrlholf
luch ICA. -1, 1.1 not -
-cimls %%ill, volnj.l~~
rpliflifille &TIM I'm m%vol k rA 11% 11.14 9. PACklili
s, _UL with 11F. With il-t-4111% 5 IlrN. usital tile wt. h-ts
own-A,rd 1.1, it., (lit oo%t luml,l I *, tit, it 7f, '. ImwlFc,t
Into iml ~c. 11,0 oo(g. Ll~ C. 'NAf)AC, ..ml %t,1 Willi
"ll"t; tl"Ill "i flit"It"If fl%lllilc Kivl' 17 V; 3,41-%tt(V
0101C414COFt (Vill. I.. 7~'. " (it 4% ,,tI
1119 261. VIIln 1:)#Ve. 10,11. Willi ~.l Sit '_W IICI Ili Cities
ujsll 111.7 si. Mr,CIICII,Ntk a f,-lv he.. it Is' give, S4'~
C.11,C4 16 :At Ill ~ 11, tVIII). lit. 141*
pe,tot, I it. Vitt Willi "s,% .141CI" r~ 111K
V-AodIw livid, M. I'. I'le.ktoll I a Vill .1~~
S(KA, With tre,,,.,1mg i .... I et,pj. tile .,I I.,. ~%j , ill,,
94.5e; vwiillic avi,l, tit, x '. Vill (:j I..,. V. ,
in JA) cc. VtOll :111,1 1;9 cc. li N 111.1 ill .114. Eltill 1,
h I 'tirliAlrd fl hl,l. ill Ilw ptrwwr of 1-1 it. Pd.el"I'ad
N it Is
), tile 110 llentralilevi t 1111 NA ill. tile 111141, 1f.f'J.
ASIA tile filtrair to oil, v.. Ill.). Wish 17'is c. )Ili
41111 hYtifl-AvIlAtell -19-1111 -- lit', Wish IX. Kilillf , J
islet ho% .11vilrox V -1 -L .110l'-plic, It I [w 4 10.

I-i'V (X'?, Ytihllti-ll ITYOA14', Its, 1W 7W1. SI, illyl.amol
-4 X wt Is C I If N, givro I Iw I -Nfe vilot, tit 1:111 W ; -If A,
detiv. Mi. Isrclut, with Ac 0 C,If N it "f". its it ',
farMitist Xf W fin. with 4 k Ito i"i m. -11:1011 it
isisdulipti. Tivatina WN15 If. X "fill WRt -v~ Ar,I) movs-,
1.7.1A g. N-Ac dirivill. (XII). on, 142' 3% which, tolu%M
1) 111%. Its 2ice. Anhyd. E1011 with II'15cr. 1111CII'Milld
its. Ftlt I C. 111 0-
I's
EfOll Ov'stv'Iff.5 lit. %fill Ittoth.-r--of IX
Ill life trulitm ptikkict kirld vkith Av,il-C.l N hi~ ..%
i~ IFIA'doli-of 11.2 g. V, Ill. IlLf". vid-fillit will) IM Ill
FI(III Ilir II-Aedryiv- 110 moll. iw IIQ', %loch -file fill)
IV 13-methiony-I -1. fogirl"ttv -ill,
U10', *tIhAf-,I)Kv- 111, 1.. I:lx'. K~p
iligi).113II.V %ithO.Wtv, N 11cl~.4111t, at LW.tfld lw.tf
till; the Invit, I lit. fill it Strain Will xi-r .4 itme, 4 li-
1whitts, lit. ISI 7 " vt hich emitfol 1. m 1. 1.
bv cryou. Tovastitilt OAK5 It. X-IICl :1 hr%, ulth f# d v-
N Iftliks at*. FtOll sivros*21111 fit&, NIIA'I. f-SmA Ili, -t
Ilvdi'llilille drAvaltr. RefIrs,finjt littIL! X X.II%*I lit som
willill.1"Siv. 4 SHOW Illm. 1-. 1`1011 sm, a mist, l4
IM4 .14'. It

PAwtive of kirta siddliblifils, Gkux~
Was" florisr. 41;41 tioluji Klivilic!i itniv. fi/rxrd,
I. 1149)-if Xim. Faly-4ral $6. .11 Ily.
e*14- %,a,- s-olmhu-1,.1 tit 16rifir I he jumlwalains (d ills,
-4 afth ulkyl.
~tniinroo. Ths, hi~ulfite t-,,nq.l,. a 11' 13 lirl., All1rhydr% Vital,
Mtilat4tll tOACid,41111 Ali-41h, Now nst'. g.luclivo: 'twoo-
dctnoati,mi wtills Alwyl.aminv- Thy litillialy tortallics, of m-h
1`13ndell1`4110"I. "try 14ILY1.41111mo Ulftuliv .1cid" shing (saw
1-yolfullrowily,oi% 'ilkv defiv,. Aryl-
xlyo%.du Cents. lit, oil x1mil, 'Indif unt Ile colitirt"'I %*till
mnitux kritan" wonder lbe ~iunr mductitm conditiamb. The
6,110.ing cimwlpl�~ %tro. tart 1-1 : P-11OG11.V(:O)CI1sX11.l1r
t I a. In. IfAl', oa, ObtAntil sit yicltl bymts. with I I a
~u.lwn~iam 11 15 x, imki,t Rmiry Ni ill is) IuL 6% Ptoll.
"Iduls J.7 jl~ Nl,:Sll! in v$ till. I'Mil, .11101 -falsely adding
:.N." ant. tit A ~411, of 17,7, g. J-110CAII.CM110 ill FtOil.
file relu4:ti%r w.i, inAdr its a in-rLd app. lit
45, with a rutAtilis Slifil't i:l .'ON) 1 (241.1) 1.) with
:12 fall, 2KC, 11c1 in "I.. YkIded 15.3 g. 110 mit, In.
zis.. M), no. IM-20". wa,
musilArly obs;Ainett in 16.:4. yirlal toy ticAting 8.76 S.
RUN11'. .4%, Aitave. adding 15A2 ff. cryst. 11,CSO., filtering,
di-olting the lips. in 140 till. 2.5 N K011, anti uitS. with
Cfj~; the HO utk, lit. 6% Will, cobtaincd by d6wAvis,
11 in 1.1) N UCL P.110C.11.0:0)CUSS1111k UM in. 158
va~. tablaincil ill . J).N. Yield by ;adding the utoll tiall. of
W9 f. p-ll(K:Jf.Cl:0WllOJIO land K. (frohly-&t&
Ph.NlIj law a snqwss~im of 7.0 j. Rmicy Ni in lUU nit. 90%
J-4011. slils,%; silt l:lt lit I'm Ill# its[.. trwrAting as (art. filtering
4 the rutAlysat, rvAl-K. the fillfste to -no-third its vail.,
Ading 9.5 g. cryst. 11,CO,, filtering, dimalving the pill.
in 43 all. 21.0 N KOII, atut satg. with COp; [be Ila Idt,
sit. 21W, c4 III wal, obtAined by arryalm. from 2D X IICJ-
#x-110cJ1.c(:O)C11,S/f.Vf (IV). In. I:N,, WQA Obuilled in
1,5-1. Fivid lov tirliting's Su'lovilbitail all 11) A. H"*t RAnCy Ni
ill Pit, old, PO" F1011 " ith It. 'Ading l,X5 1, INICNII, in Ila
RoL 00111 AIM Ill) nil. 11.05 JI m-fI(K:,ll,C(-OPCIIO its
F(Oll. hydinsicuAling it. I'll 1, &aid trvAtilig (anther As flows
III; the I/C/ jail, tit, Z'94', cal IV mas tibld4l"I by Ittratiod
IV with 36". 110 ill all%. N1011 and riymg. flown walct.
V. in. -444 m'. %.m ()btAiurf
in A-34-S. yield by tmiting 1.9 g. Et.Xil, ,,, fW IV; the
HO 144, was ubtatintol by rept.4ticst c Inilfrom
2m X )ICI and awatcr. ,.,v me.-
J C:T
/M V1. ill. 241 ", W;i~ ubt wined its OA-S. Yield by wims. -till
It ;i %ulaparnsion owl 1.5 g. Jtlivr C fulag. 14% load ill W) in).
E1011. addiog Lmi g. Nf,,Sll, in to) nfl. 1;1011 laid .30 nil.
M 3A-(llOhCsll.Cl)CIlO in 1,4011, hydroilrumisse A-
all,'vor. lit-uIrsliling 'Aiti. `tJo N IICI ill rtoll. fill"ll.
rt.,Pg. 1114. filmlle lmluw 30* in A Current 44 11, dit,"Ving
the ivintlue lit :14) wail, v,.itrr, vitrifying, emoluts %till it-,
S49. With Sll~afl~ 110, Waiting, J1411 UAlibillf %ilb FtOll.
EtAlioulas4ittioitliFfOll. JJ-U10hC,11w(t:0)C1h.V1I-
C11.l1eJ1,,Va, Vu. lit. :~13,. WASuhuiurd in 7.1-K. Yield by
treating 1.1i g. i-PrMIS ;1, file VI, filtering aid the CJIA-
lv,t. nentrAlijing the filluaN -ith ',.a) N fftWX. in Etolt.
OAPS. Ill S%Ulafo. retain' ills the imalturc by tv4ps. 3 tiartar,
oith 30 nil. all,. EtOll. Awaiting the t"iduc to StAnd ever-
night with 2o till. alt.. RiOll in i tefriso-r4mr, 4mf uj-hing
with cold ab,. EtOll SinuLr treAtsucist uf.'J.4-(PhCIIt~-
C#IFsCOC1I0;JuXA%vVU- 1o-I1OG11.C(:OjC11O.KIIN~.
(VIII), w&,, obtain"I in yiclaf by smiting 17.7 S.
P-II0CJI.C(:0)CIlC#XllSA. --'Is sail. mairf. And "".:,
g. KqSOA %ith lict it pit 5, anti Autawing tit

't'And :414 tirs. Vill wa% "1'0 0.14bled in =11A.S. yleld by
lefluxing 24.15 S. crym. p-If0CJl,CII(0II)CCI, and
.20 Bit. water with 15 X. (~klr%v cacOll' allowing to
-14nd a day, Owing, adding 2-J.2 g. KzSrOt. and allow-
ills to t.nd 24 It". A 30 wt,tholl "nist. of Clarify.
olic uith iwtivr C air aq. v4tt. tot p-II0C#II,C(:0)CII0
1.1 C.A, 4J, 42414). ath ril, .11.1 S. KjASO" then courd. IICI
M tilt "' allowing to .1allil '-,I ht,.. and rry,tg. fruits water
in the pir4cuct -it Kj$().. :-(j-11yl1rexypkcr#yI)-
Y01111=4211JU (M. In. !M% %%A~ obtAilittl in 3.4-C. yield by
I.ading 6.4 g. Vill in 65 mi. bot witivir with 2.38 S. P-CG.l$-
'Of')l I." loill.. ;l1k)'Allig 1.1 'IL11111 .1 day. liftefilix. anti
,LjV.tg from '111. N144111, IX na, 1ri'l.lot it) Smilt-fal anti
'Wor Arld.. alk.1114" arld aild
I :01CHOARA0. (Xj (.".6 , .4 VW,--t Iftly A4. ubtaillill
I'Y CYAPS. the aq. ulu. of 01-110c'If. , :0]iCII0 hooduced
front m-ll(-K:JI.AC by axillizinx with Sc0i (4v. cil.)Vto
X. nd., adding 22,2 S. Kv&f)& in 74) ml. hot water, adding
conal. IICI to liff it. allowing tit %land, anti crysts. firm
-Ali-r. (XD. was oh-
lAucd in 75% YiTkf by tIL"olvint -*-, J(. Vill in W MI. 18.6%
v
MeNlis mAn.. willing 194 Oil. 84% EtOlf.atInwing to stand
1)"rTnight, Altering, anti washing with 241 mi. MeNlic in
EMIL P-110CJ1&C(.0)C11GV111'k).W.K (M), m. 239-
41' wa3 ubtaintif in SM71p yiehl It rt-Auxanx
27, j. Vill, IIIJ S. Ir"hly-tikid. PhNift.jud 171111. Water
.0 Suitt.. all-ins 1. mmill VvIllight. c6rifying with 1%
-.4clise U. 111irring. I-Vilpe. Int ;llolhrr 1111tiur. 111irring, Anti
tvinhinilig both I)Ilt*. P-11ocJ11,c(:0?01,N11Mf (11111.
In. 1411", WW% Obtained in I 11.7, -1:. YiChl by Vitt. 4
4 Wig. Raney Xi in:1lN)juj.h4!; fitOll, uith fl.disolving
~-N 4 g. X1 in 1411 ml. watri. ditc. to 215 its[. vLith 84%
R101f. tre4luLing a~ siv~6NAANIVO, 047fing Off tIW ClArAtrit.
11VAling the filtrate with 11.5 S. 97% Ifil4h. alkiwing ill
ilt.11111 uverilight, tilli-1411. diViOltilig Ilk' 11111. in 121 in).
water. clarifying with ~,~ act.%r C. fillirtunt. und utding
-28% N11,011 to pit w.'.,
(lav), in. 100". wj% ubtained lit tLK-j. yietil by atg. with If
a suspention of 25 pt. Ranry Ni in :1101 ml. A)% PtOll. .16-
lailvi is :14.3 g. XII in I-10 Ull. lukVitarin "Atrr' 1111C. with
K0%1 M011 to 215 od.. rtilucing a~ allove. filtcring off the
VAtAI"t. J:VAPS. (11C jjj(f.t(V 14 flIL1.0 111I..;4.11fillij 3d.!t
X. cry.t. ttc4o.. allowing to Wtd %4-vi,rAl '14y'.. fill *
and safg. the sobi. of the crytiah in .110 mi. ",11 N00i
with C(h. The F"Iuctivc "imirnsaticin of ilil without
%epu. ill the hittintr6tir ptojutt gave 1. lit. 147' (tbii
-.Ulllplc vv.ts shuwn to Ile "identicAl- "nixed in.p.) with the
previously larcpd. sample of 1, m. 166") in 11.7-C. yield
by satil. with It a suspension of 17 g. moist Raney Ni in
310 ml. 84% EtOll. dinolvin parately 27 c. VW in
110 mi. water with cooling. aildisneg 7.75 C. McNill sla a
40% aq. soin., di'16. vich 94% Et0II to 215 mi., ailding to
the catalyst until I tool. It isaboicixii. tiftering off the cats.
IV't' 'id.1ilix.,ili X. S-""r Ijjn' t'. th'. filit.ov, chilli,ill 21 br,.
in ilk' ruffiscralaw, filtttilic. ill-Sking tilt 1-blitt its ~.'10 OIL

Acyl MWM*a 0 - N im 00 Ambremillimliffilt 24=b"?-
basumisitse- CAbor Fodor and J. Xim (Univ..
Hung.). ;. Ag-.C4Fm-. S;pc. 72. 34W7(IqaO).-
cm-2-Benzaimidocyclohexanol (1) (2.5 S.) in 8.7 cc. abs.
at 100.
KIM and 5 cc. 6 N dba. 1,11011-110. heated 2 b".
1 4111%, unchang"I I And 441% CIP:'d ' WW71
It, :=*. Tbe ardmi-imm"W"OMM of 1
sinillasly lives 43% tecivered Ell &W 49% Of the
isomer 0 ) of 11. tn. 774'. U (Q~M g.) in SD cc. HeO,
ttested with 0.65 cc. N NaOH, Siva an imil which. m
4cratebing and &Mn. of exerm alkali. yW& 0.173 t. 1;
Mix)
It. IV with 0.9 cc. SjOll save an oil which did ntx
crystallize until the further addn. of 0.6 cc. alkali. W14M it
yielded 0.120t. M. Ilie intermediate oil froto 11
sminmyclobesyl bitimlle, which can he isolated by im-
mediate tosyLstion in 40,16toth, (V).m. Iw*.
m 6101 lit tilvv. llpmO
0.14 lit I m. AAII.. titi-t with vuv,ti
allut give 0.7M C. W the X4oj I J"rv, (VI), tit. 1&0-4 ';
with DzCJ in C,II.N it yiekis V. I'mmilarly 1.12.5 c. IV
yields 0.9 1. of the Irani-tiomirr (VII) of V, m. 1684W.
The fram-momw of VI. in. M% gives; VU with MCI iyt
C#H.N. A mechLnism of the 0 - N acyl migration i~
presented. C. J. Wtst

caleftweliftel awsladeft of thlaramphas" with IM, I
i-elpbodrim. CAbor Fed(ir, wt Kits, anti I%tvin Sil-
ly. ~ - - jr4cfMal Soe. 19S1, I$V"T
!tVZ"cen==r a"Ltiml drriv%. of rhlfwam-
ArnitVI IP-04%'CSH.Clttolt)CII(NIICOcttcl,icltoitI
be" proved by Comparative *CA Mtrwiors elpt's. to tw
a
klenticul with nor+epWritw lPbCll(t)l I VIC N310-WIM.
M 131-2'.
""its Inim the Its tforiv. and AcO (2 bri. it ZNI). Ph-
CII(OlOCII(XIIAOC160AC (1-A a.) with 15.3% IICI In
Meoff (Owtrwot) gives
17m IM. PbCIf(OIf)CII('%Ifllx)CffsOAc
2 )14m
0 cc, dioune anti 2 cc. ON IICI In dititane
IW
111W I
giv"
-A a a. I.J.di4twory- I -(P -d"islop4eaw )props a.0la
). delig f I froth, thrmigh the'lLizo rr'.Ction in
if. tl~ 1, 1,51. ViAlt 0, Ilk! 0. of the I-Ph dowtoc, M.
I I (* s. CIf(OH)CII(N'IIDs)CIfsOII (70 x.)
a 711, Cl In IN) ec. C.11.,%,, heated V min. on the
Olftris Wit t!nd'l. it 12 fire. at 2M, givv MA a, I -k Ucis-:-
(V). lo.
70 S. T sinif 18,6 cc. Ac.0 Its 274 cc. CM&N. heAtnt
30 min, on the ateam lath, kept 12 hn. at 24'. clibl. with,.
&V cc. Cgi. and estd, nKvmivcly with If,(). X IICI. and
If'o. ent". to 223 cc., and dild. with WN) re. peir. et her,
b~1-AcdMP.(V1).m.l41-2*. V(2.71g.)
rns"Aoalf'.N, treated dropw1w at -tO* with 4.6 S.
MeSDO la 28 cc. C.1-41q. krpt 16 bra- dild. with 21M) cc j
ether, mA waslierl wftb IfO and dil. Itives f:k ~-4.
tn. 113-14'
VI ( 1, 1 0 In 2.14) iv. .1"Isvil. FlOfI anti 4.15 re Jr. .1 N
I ICI, treated (70 min.) with tj 1. Pd4C &n4l nentrali&eff Will]

A
comewation of dissitior"awl"k
anot a a soled slitchasshan for acyl trifigrafim M-0.
Chhur, I'M* -410 1. ki- I Viiiv. Stravil. Aisne.). A
1% I.-hotam.4 In 4*, i%.1% 4-11jainosi its 19-1. virl-1 bt-
torminji . mr.l.-smi Ili X .-AvNIIk*.Ilt1II it 44k) sill
Utt'll -till :KI is ~rt It v Ni it, An ki W rusu.
.4th 11 under to ?VI log. .1. vIll. pte-wire at INP with cull
linucvt1s shaking, alhm ing to st;tn,l :.1 lows at this terrop. and
1ho,filtrate II t%itu.. it 3.1-40% Hold
I.,41ing the re.j.11W 'Ailb 114) till. WX04 It% 111111.
wl"Airwa.4 1111. In ISO', wastlidainvil fil 17 It
Vu-I.I low Itillmns; Is is 1 .1111 1141 till. lm-'j, lICI I., Ill-
1%,illil.throillill .41110, So fill 14.4lit 1413(41 1111, and lWosairl",
Ing lov the timlittil,
a-efd'-wh4evand till, 1.~I, i'MAIlle'l bv AtilnuilIA"It,
4hIl-ttWV%l41hr%Aljl%l. 19111-tal Joy A %-hill It'll. I t,111filarn
I*tjoniviathm rJ floor ausim, dIc. ut"Int'"I (4 1. Aftst-Cou-jan't,
a I) . 1' 1. 43, zi - I A. Ife,11VAI Wish 2 9144JC
IIVI. 11% dl~t#-06hr~- its. ZW,
wasoblaimcd. 11 the unit of IICI added wissiviffrAssed to Ill
tir M incolvot. the yirlqiv %%ere .12 and W%. remp. Similar -
"4% trotAtnt I., Ill,- njA jul-a 144 2 to,. J- I It'l w A-
'utlivirut It. ri to. It a vis-11 to, to ,III- At. InI,,f
I'll-trol lov O.willuld 111.1t dw IATI -1111t N -I 1 -111, 1.1
orpi. Fll.t till lill'table A I,
.4'sly in iminloollAr '14 C.11, Ilit.
alciintspl. or t"iratigmi in jo,Jjr ~,olvortscv tic lov hrating. bt
AIC. the equil. betvicell uIllitle 41141 Aluitle ~111 I% Shift"I I-,
Ard lise anlidr, .,1,l ;us ru-, J JICI it tit.
ailli'le %;dt. I'llo. lou'l so1q. A hr A' %I 'Itilt 1, .,
mrill I., all Is-, Ah. oil, 1,11, ..1 .1.1. It 1~ J, 1.1 1,%
lilt .16,Lsm'. llmt,mlik"K kll.~lj-
111.1aill., ItirtKII-11 lilt 4111MI11111till Illav A%) r%plmll ill,
not, till I'loct. ill an im 111111111-tv .14 it IllidtAl 14"1 r trot fin lin,ki,
likills, I he imiki'l 41111'.14 11".. 1., 1 a ... I Illo, I it., 4
",,vl toliar.ti-I 0 file
11,1141nolso .41 Itot I to mp 1~ 0"" Otn'ttil,

Cozifigurational correlation of pharnlaco ti,
logi
alcohols. 1. CouversIcin Of X-MOtI1Yl-DL-Cph.Vab into-
UL~tj)hedrint zad 4,-ephedrine. GAbor Fodor K&t)ly
Kocrka. and UuJ6 Szeke-res (UniP`M~- -~WM
Acad. Sci. Hung. I, X77-84(1951y.-Phartnacolog
lea
DLetivL- Dt'N-methylepiltdrine (1) was convened
t!3,wio-06-bejizoyl-DL-ephL-drizie (11) into im-ept f, L
tedrine, (1a)_
anti f-epliedrial: (IV) providing prod uf the r"pective
figuraticlual mrrulatian. ISzC1 (15 g.) was added. to 1 lw~
C&14. und r a-ulled, to give 0-13% duiv. (V), m. 751 afW
5~, P11 crystri. jv-cy"oderiA-.O(V(VI),fn.78-0*.%-asobtaittedfroft,
p
gave 111 (.1 r.), m,72-5'Jrtxrx petr. ether. I Z ,
with p-N0..b7.Cl gave I-11CI (2AYg,). "3.. 204-8% and I-
ill. 78.-Hl*. EvulliA. fif H in vacuo followed'
klYclx4jilgin pctr.t:thcrguvc 0-(p-_N0,r4z)ldcriv. off, T81%
Thermul dtgy,,,&tioja of I Wlow~tl fly adiln. it
of NuG
NfUr'N'll ui proved by a zmli~d m.p. detu. of its p-Cll,C,
U.SOL, (4:6v. U w.,%~, retluxed. uith 110 and tzeated -with
c,
I (VU
Work e Ill. t,
235' frota %EvCL
IV, io~ 117~* was prepd. by.
b..)ilillgVlLii,iLlil.77c,~N;LOII. III. Conversion of bt..obr-
eptictirlat Into 4-hytiroxy- And 4-miltboxy-DL-norep
hedrine.
Isi, tvu Fcbtir. und Dczsd 136nfi,
p:tper (!,A, with flit c-orrelation of the*
cuilflgljratii ,m of (1) Nvith that of.
'A'Ith tl=t TA 1JL-CPhcli-
rine, 11 Tli'mit~'iln.6 K.) kidded with mirring to cold
11 %0~41ZSO, to give nitrate (1.65
m. 247' (from fr,e bwc (III), at. MI)'. D
Alt fiv. of 111, ris. 1050,wai vr~-llwd %-ith dil. j6(l ~lrjd 1120mid
mduN,4 N~itb Pd~C ID /1' 3111 ill 0- N-1 WA 1!0~1-1) L-1101`~'JAIVIjr ~K
y - -uL,11
t_jiy(jr,)x~ A'~Ilcuzfjyl QrNdicdr~ixe
ill. 176'. vut, lirclid. front IV witi., MNO, alld inin,
Aviiii UzC1. VaTia
thu M,~ ethcr (VI), ill. 101-50, (,frxmu
gaveflte i'n. ltrkl' (trign FiCill-EltC) thul trot"
11j.p. %Vlltll I)IIxed
'With ILL- IMmIllit rlu;ll UW~ b-llZ9Y1,1fl0n Oi

01
OUS altration Of
.lio
LIE kin z is -uroimi-~
&MWg, PIZZIApt (1) to 5M X.,
ddn. too 111
HNOs . 1.6) below V, stirring 15 min'.. antl jxxtring on:
ice ga an on which crystd. togive 75 X.-crude 0 S-dirsilra-'
allisok (11), in, about 60'. 1 recrystri. frorn M;611 gild I
from Cafti Lrave 20-4 g. yellow apedles, m. 95-7*. - 11 with
Na3CrA and HtS04 gave J,"inilrophemd, oil. ~ I t4-16*.'
It hydrogenated over Pd-C In MtOll coutg. IlCi absorbed
'102% U (Wed. for reduction 9(2 tiltio groups). If(S.8j.)
JW2.lml but AcOH udded to2O.8 g. Sit d6iolvrd byheating.
ill 108 W called. 1(cl and 24 mi. MO, (lie mixt. hemed I
b.9 at 100", cooled, made alk., extd. 6 thues with Csils,
and the exts. evapd., gave 5.3 gi_ black oil. whicla crystd..
front McOH to 1.2 it. 2-atnino-4-ni&oanisale (M). Mullitei
crystals, m.- l1ri-17.4; acetyl4ted by AczO at mom temp-
to Ithe N-Ac deriv., m. 178* 11 (20 X.) In 100 ml. EMU
~'trwtcd dicipwise at 100* Will 1i mi. wfol'o and a Mi.
MOIL in 60 tai. IttOff und heatLA 30 min. more. gave 19.2 K"
q.1-(OiNhCV1sN11iV1h, m. 10"9 (front CJI,), '2,4-'
~1Z6,N)iCllANllN:Ch1Lt. nt. 126-8*. Nitration of I as''
t if Cacont i ;
!aboveat -5*6veahurrs cut' eV3.4-0~N(WO)
:(IV). T mechanisin of conversion of ItoH Is belie-ved to;
.1,44w
Involve nitration (A I to IV, Oxid
devarboxylatioll to a-hf.eOC4lf4NOj, U"Ll nitra-~:
Richard 1. Ak;twie I
tion to It.

Synthesio 40 tibia m~dnnd1%* sad a relatod tmln* alco-
hafg. with a ~ Odmay, Alut" Uwe. , ckbw Podori Odon
Af4d; _&ii 11sixt. I. 39&-Mt"l k Eflefsh)i-A new
N-Submitutto atnlno~
it". Statthit with hydromyell" Total% Waii tmended to
itomdroaftna'andst X7js-HOCJf4COCfftNH-
,CH$Ph -m. 131-20, wix by reducing #~_-HOCA.
COCHRydraw or Its X11194a.4dut. product with Ramy
NI in, the pm!*nceo( PhCH%N1ts.' TILeProductiwerektril-
tical 82 and 79%, n-jo,'_ Rvibirtimmot
jusmil M Cavi -PhC!FsNHC1fvC1I(C,1f,0JI-Px?lj
Jll excellent yfelif's by rettacing (Pdec) the fict silts I't I
Rtiticy Wit) XWelt 7;1
NIIC.FPh,m,
(ton of It over jldmc PVC normitenalilte'(9,21% yivltl),- lit,
1&9-9*~ A' mixi. --of 3"4-Mr(XIIO'C.IIXOCIIO-KIISOj
'aild P11011mils toil,, 3,.1.
rettuccif (Rnuty NQ In give
,IeO(llO)CJ14CI)Cl[iNHCIItP)s.)ICI, (IV), ill. 221,21'.
Reflurlivil (Pit-C) ot IV Ruve, jIj'N
'~Vh'tn. -120'. Was -firefitf; by: rdluxiali 13.4-M! N11:0)-
i3fiCONfe with Wh; - 2-(.*I-lfidrovs--i-itictltox)i-.~I icityl)- i
Tsinoxillitie, mi 143-31. (front (tit. hWfl), was lirciA. from
und o-CJf4(Nffjh in hot aq. solo. RjAuctlim (Rittivy
NO of Twith PlicifiNits ave 3,4-II0(MeOWICOCit,-
NIICIT,Ph (VU, m. 236 ((rot,, Htdii). , Lower yit:kfs
weire obtabied with thtt Slyolial In stock sofn. HjNCtliCII-
170-1* (from McOll.
Et,O) wus lirml. It - reflucing (Pd-C) VI in MR. - A
MiXt- 01 P-IIOCI"490CIIO.Kfii%~aad'FtzNlt ulyimiled
I osole of It (Rxiney M), but only A hydroxy lixtem, pm
lwnlably 1~110C,114COCH,01(, was obtained. W. T, 8,
~201W'
-lava
71
a.

Gemb. I. KWMb. Va.
Kollouicb. Va. %
rein, ovach (Srefted $tot* Unly..
lung,)- ZAAF. Ohshtliel KNO. Gen. Cbea.)21. IM7-
I
WM 1951).-Tbe pytiouldine synthesis frolen estm of wols
has been 4111lendett to eW ethm, To 23 a. No w1r, In AM
ml CJI. %a* added 83 g. NtOCIIA3foCN and Wig, IICO#Ht
41 M-110; after a brot, the ppt", of the No "Oble was com.
*It: this was allowed to Mond :1 days at 160 the tallit,
treated with 125 E. JkIrK%, kept 3 his. at 63'. 16tered, sold
lbe filtratr disid., yielding 12-3 a. s,-ndjmwyxWAykxjp-
dbexypr*PsrU6k (1), bi 9,.-S*, b, 64--71 ". It, 71142" (the
Axn'r an the b.ps. of the 3 tradi(xvi, all of which gave
analylkes clormponding to the abm old orte appamtly
composed of the 2 jeaux-trical Isomeric structum possible
for the product). The above Na soft sepol. by clentrifullitig
aud treated with IIC(OEth in the pmecrAt at PbSOtH in
#Wr HtrO readily fortned the -alkaxymAykne nad"
( ).AD Oil which was IM purified further. The No loolt
witb P-()oNCJ14r-OCI gave 60% a-p-naralot
m. 1M-10" (from CJ17"IM(d2hi
kind 1-15 a. AMtAmidille ift HIM let stand 24 hn. give a
VW
I-PlethvW-dwoo ejk"YMfjkYj)#Y'j"'jjiaO' kxftttd as the
ned from I and at4tatuidine-110 treAt"I with aurotalulol.
tai
knit, o( MoNa fit abo. F1011; the twooluct may be iWint"I
&% the 110 mit, in. !M' (fruto BuOll). The &After pr-
cedure with HtOCIfjC(-CfIUAc)C.% and actlauddint-
IICI In CJ14 ove aceftnoidine "404M, In. 1&J-60, and a goutl
yieki of 4ijof.
Himumertat (21 at kro 12
after okublintatkin too vurvoo. In"
bfv. at room temp. with 4.1 1. N4CN III 4q. 111011 In the
presence of Nat appurrutly dw not react'. houtind IXVUWI~-
acetal with KC'V anti \at in 14. Rtoll to 75' pvv only
tram of N-conts. product-L; no ither did bromoucetal react
with CuC.V (at besting, I)ictromite oxidation of (1310-
C11twiloll gave h,, 93'ItIV.,
this (j4 a.) shaken with irmh Xall.94 Soin. and rild. with
RW care on oil describcd as tht: cyarlohydria(?), which
treated In the rstO soln. witfout purification with ArvO
gave bs 10"*. No
satisfactory method 0(ckavagV Of UM AC group was found.
even beating with PA and FOCIo in p It" gave only
-toc"t OIIC.Ncwm
polymeric Ildimts so that pun! IF Z
now. be prr4 G. M. Kosokpoff

TU qnth"W *I tftshydraimoquimWise slitakil4a moder
cmdidmc 616n Kovics And Gfibnr Pxl-w
Isex"I. 1 Unx ), C"~ fier, 54,
klecaume%doofine, 1) AlWAY4 tx-cwv in I he plant as a racrtnAte
and is thrmfur, V bout the action of en-
XyTor%. an attemlit is made to Synthrske I from 1.4-lio-
4 mro)(ViScUrCHIN111 M under phokil. ettwmfitiml,~
Adding 40 a PhClf,Ntf, to 45 X, 3.4-%ic(XII(1CJI.C0~
CHO.Klis" in IP40 cc. 11A). making uptbe~,111, WNW rt-
~th Ki~' . Etoll, AddinS this %oln..drkvwiv anti with vig.w.
Oil- Muting, Z =- 4 ~ VWt JhAt I m-A. If is misnimed, ttv 75
g, RAncy Ni in.isl vc~ K3% Ettiii livizmoly ~ttl. with If
At 45% Acidifying Or filtered sttlsi~ a1c. itCl.
"me&. the vAn in rut as at W* to 0,A) cc., anti keeping it
24 Itts give "N"".
110 (Ul~. in. '-'W. flydrWnating 15.4 jg~ W in -300 cv.
97.5% Acoll in the pir-ence of 5 S. 10.5% I'd-climrstal
until 2 mot*, If we alisawbed (19 firs.). addins :9 cc. 7(or'
JICIO~ in 30 cc. ALOII. and coutinning The hydolestAtim
at 85' cAu-e the Abonition 4a 3rd mol, If in f% inin. KOAr
in AcOif equiv. to the aurt. of IICIOs tneil I, added to the Im*
fillered %an., which is filuzird Again. acidified with :'* cc,
evned. IICI. and CV-Apd. im mcme. 911rins N1 14-Mcok-
(IV). . 24 pievak.
anar-yeflow MNIA14. in. 197 K*). Adding I(M jl~ 3.4-
-U(KmrO)C*II,CO3-IC [P7 1. in 361" yield amigding to
a slightly nu.tifird funn the vnvtb~d of Schneider and
Kraft (C.A. 17, Mol to;-,rj x. SrO,, d6solved in:U%s cc. diax-
aneand 11jer, 11031 W" frauxing the "3i%%. CVIM.
ibe filtemImAn. im rormo. stirring the residue W Jim with
'491 cc. H.0 im The water bath. And conell. the mAn. xivv a
,irup cetnig. CA) 57jv 3.4-II0(MK))CJI,COCJIO (Y). Ienmm-
yellow nrv-Jk.-,i. in. 120. Adding 1 2 x. a-CJf.(N*Ift)2 in
111,Lv, him 11,0 t', 1.9 a. V in Ill ec. IIiO Xivr-21.19 x, :43-
in. 1421 3'. Reduc-
live vot-OlensAlim of it, it. III)CII'MI, Anti IK S. V in.,01CC.
EtOll in the pFt-Wnt-r.,f 2:, X. kArity Ni 45 min. as 45' as
dewedicil above giv" -,47.
C11,P4.110, in. 2W. which 1P.4 g.), on further hydrt~
'erl"I i"I.- 9,217,
Kcnat ion, il v~ffl% ~Iulcl. in. llo*,-7* (pirrek,
) JjIlCI,jV.n.4-4MeO~-
C1.116CIIIC111%IIIACI (VI). 4-IRXJI.CIWIIj-NIIt.I1CI
(VUI. JIM .1.44110)tc4lljclflclll.\Ill.llcI (VM) are Coo-
th:nved with AcIf untler conditions used by Scbug &M
HaMle (CA. 20. 14:)),). A -A31a. of O.OM mol. amime in
-'it c,- 11,I) wi-I X, iv N Acil i, awd, Utv t1b ~A? CV-. kept -,-'
lits. At:211' is ith the Aell vititent deW. every 24 he,.. evaW
t4 V%A Sd~ 4t iidi'. A90 it lkill V%M%VttM itltil the tiit-fAtC anti,
.SAIVAinc 1XI 3' - viCTAtv, m. ;.,V" 5 .15, 6,
vi'vIlk"I'm W.9 tpierate.in 1-0.4 ill',, IV, WAS7.1
~4'1 xi%.r twmiuct, F I., IttAutt,

GABOR,-Fodor -
Decomposition of
Chemical Abet.
vol. 48 No. 4
.Feb. 259 1954
organic Chemistry
c 4 M. a
eld by beating 4,6 AcYH NHNH
th 8 mi y p id ne and I X. freshly didd. M
I in seal flask I hr. on the steam bath, pouring
the liquid Into 150 ml. water addUW with a few ud. H*90t,
and recrystj. the goduct repeatedly from 80% MeeCO,
and drying t at I '. It seems that It un
ridine disproportionation Into 1, thus widA1Vlt1n1,py_
.the reaction with McCOMM. This appears to be con-
Armed by the facts that (a) YJ yields I hi the same eipt.
at room temp., (b) 1-a"tonylpridinlum chloride Is foo-
lated frons the reaction mixt., c) U affords I hipyTidine
solu. (slowly at room temp., readily on heating 24 hn. to
401). No N evolution was observed when the latter ex t.'
P,
was conducted in a scaled veisel In a stream of Ms. it
was surprising that H, a deriv. of NHjCSMHNIIs. should
almost spontaneously undergo cu tatramol. aKidatlun-
reduction process. It appearn that bath the NHNH and
the C811 groups confer instability upon the NII*CSNH-'
NHs mol. and the decompn. it probably very complex.
Istvin Finkly
io

I
r
,
f.
'-A
11
l -1
ith H
CO
0
n
C
O
M
Q
Abst -
.
l -
tt
r.
.!.
.
L,
A.A
,
, %
,
H
C
.
I
. a, also
r~crimtg the proInct (mut 2~( mL abs. EtOlf,
Vol. 49 -NO- 6 `,7ii 0-:41 (5.2 q ) by shiking 6 hm 12 4. M,-tC: -
hT
t
5N TICT i-
C110
l
72
l 2
l

1954
z5
F
i a
~
.
.
.
m
m
j, nu
atm MOIL
On- Pr
~!i .:t fr2in, 100 ml
diaxaae aq4 r~vrI~t
:
AT
o
Chemistry
G
d .
.
,
L
To prove the sit-vctm-.- )f I v-ar ni~ -%ptt; -m ont.
c
rcar The mcrcaptozri "It, azol,
'
siavc 11-
~,v iih O.."DICS11.0
evidence. of the lwe.~mlcr Ofati. E;-f grotp in 1. 1"r
deriv. de~criix-.A in the literit re has propcrtwi dfi~O-IMz
from th.se af 1. 1 'ith Phe Clio
f
h
-11,
With it high N ,ontelt, tht mpumclil forlinvi y

but the ctimpti. %%-a-s not iif~wi, it -th a of U
dc~crib-,I-l ia th~ fiterati~. A tml. ~t. aixomltng to R.,~t
'yielded the v:due 171. Tit- c-d tmc: of this Campd. proy~d
th;tt 2 N atoins ctitt be rcadily libt!ratrid frain the origin!dl
comrd.. corroborating tfms tht hyd-azrmothiazole mrm-turc

as ag. the theorcticalIF ~~We 3-aniino-N- 4- j
tncthyM-thLazoline. An
I w;" also examd. whem 11h03CHO reacts *3 NAT.

-7 In FitO
Istv. .1y

MOR, G.; KOVACH, E.
Now synthesis of salsoline. Doklady Akad. lauk S.S.S.R. 82, 71-4 '52.
(CA 47 no.14:6958 153) (MLRA 5:2)
1. Szeged Univ., Hum.
Salsoline produces a very high tension on smooth muscle tissue. It has
therefore been adopted as a medicinal and included in the Soviet pharmacopeia. The
synthesis consists of oxidizing acetoisovanillone into 4-mothov-3-oxyphenylglyoxal
with SeO . This in turn is trangformed into alpha-benzylariinoacetoisovanin one by
reductivg condensation with benzylamine and then by hydrogonation; the benzyl radiaal
is remved and the keto group exchanged for a methyl group. This product is treated
,irith acetaldehyde and yields dl-salso linephydro chloride. fl. detailed description of the
lab method of prepn is given in the exptl part. Presented by Acad V.M.1%di:onov 24
oct 51. 252T2

-F0)1aTtj-GAB0R--
$I The. sitertsocheralstry of the tEM ne allralp-Mv. 1. The
coafturation of -trophies 'and psedMI, J-
Chem. Soc:
1053, 721-3.-Corn pane'.. ffl-h"' rg tes of N 0 acyl m;-
grations has shown that the relative pamitions of the nitrogen
bridge and the C-3 110 group in norti-opine and in norpseudo-
tropine are traws and cis resp. The itereochtmical notation
Chemical Abst. for these beitijf1athioned after tbe:aeroids and triterpenes,
therefore nortropine and norpseudAropine are nortropan-
Vol. 48 No. 4 3a-ol and 10-ol respectively. N-Acetyltiortropan-30-ol (1)
Feb. 25, 1954
Organic Chemistry
and 5.16M HC1 in dioxane yield I.HCI, in. 155*. N-
Benisoyinortropam-3fl-W (11). m. 16W, h obtained by Sr-hot-
ten-Batimann bLnzoylation of the nortropan-3;3-ol carbani-
ate (111). 0-13enzoylnortropon-30-o~-HCI (IV), in. 212% is
obtained from 111, N 110. and BzC heated on a steam bath
for 5 firs. O-Acelylxortrapati-304-110 (V), in. 213-14*, is
prepd,.by "WICI with AcCl for I
oflux'" uo"ro~
hr. (VI), in. 214-16% is
prepd. by WICI with excm BzC1
for 5 firs. (VII), in. 160-3%
is prepd. front N-acetyinortropan-3a-ol and 5N HC1 in
dioxane. 0-Ace4ylrsor1ropan-3o,-ol-J!C1 (VIII), in. 192-4*,
Is obtained from tropan-3a-yl cub iniaw with W HCI and
AcCl. 11 an standing for 24 hrs. at 25* with 5N IICI.I!l

dio-aile Yields IV. IV rcarraqkci to 11 on treatment witn
2N N"L N-Benzayinortro ij-ja-ol is recovered uu-
'Changed by treatment with 1181. V1. when treated with N
NaOll, apparently does not react. I oil heating to 190'!
ruelts and then solidifies, yielding V. V. when neutralized
withD.IA1.Na0H,kivcsI.HCI. Moll heating to 160' for
10min. gives VIII. 11. The configuration of the waints.
GAbor Fodor and Mn Kovbcs. Ibid. 724-7.-The con-
figuratiuns of the epinters, ecgortine and pseudoccgonine and
cocnine and pseuclococaine, have been established by acyl
migrations and other stercospecik reactions. The C-3 HO
group proved to be in the a-position in eclionine. IN'.
Acetylaor-30-cegunine E t ester. m. 112*, gives 0-acttyl-3,1-
ccgonine Et estrr-RCI on treatment with HC1 on the steam
bath for 4 hrs. The reverse reaction is observed by treat-
inent of the O-Ac 110 salt with NaORt. N-acetyl-3a-
Ccgonine Et ester, m. 150% [a) 'a -19.4* (c P, EtOH) does
not rearra JXCI In dioxane. 2~a-Benzamidotropan-
13-.-o1-HCI 2^280, jajV -40.6% Is obtained by Curt-
ius degradation of (-)-bcnzoyM1a-ec%orIne and treatment
withf[Cl. Irefluxed with MeOH contg. 3ANalthyd. HCl
gave 24-amino-3et-benzoyloxytropELne-2HCI, m. 214-15",
lal'o, 21.0* (c 2, 11.0). Reverse reaction occurs In N
NaOH. As a.by-product in the prepa. of 1, 2-a-amino-
tropan-3ir-ol-2f[Cl lvas obinined. CUrtifts degnidation of
(-)-0-bellzDYl-3j3-CC9QllillP Yieiflq 2a-bc1l7al1lidntrolmn-41*
of. M. -'W*, fal'S W (C 2. U-0). Which does not mrrange
oil heating with 110 in Afej:)ll. CocailteourLductionwith
LiAlff, gives, after treatm,nit with IICI, (_j_*~ia.MguijjOI
(11) IICI salt, m. 270-'-,*, -37Z'; N%hilc Lj~~Jllredllc%,
tion of (+)43-Cesonilic NJ(! es,ter gives (+)~j;3_CCgojlilloI In.
131-30, 58.3* (t 3, 1-1,0) jljCl &-At Ul.
1101111 is trrated with PhC110,
46 3*)). nd pilsol I
is obtained n,
WV -9.43. NO bellZI'lidefte detiv. is obtaitiM front tile
3A-compd. U dehydrates -Fhen created will, cilloral IIS-Llraie
and coned. 111SO, at 20", flowcvt-r the! 3ji-compd. does not
react.
K. C. -&-hreiber

RM~
I Nd 7 ft-~"
Una. &A-kerp-4 atid hemi, uttiv~'- 11171.4 hot &b n. of 4.5 s, I i.'2ZS 'Ll. ~N'K301d cave with 16
-R'
R .3. tril, coned. HC1 1.3 r1tow ppt., decotap. 250 yielding
X109, '. 1002.-Reilull"02g.14Z c
CHBrCHO w
Me; 4 2,5-dijx#-S-PAea*
tion
after p
In 250 nil. hfe~CO and 8 s. C1O(M?jj* 91 min., followed by c .1
Cancel. and dUd.-*Ith lfapv~-Sls. rit"I ine, ecotrip. 201, wh h, M%ed 2 hr#. in AW,
114-1 1
t n dilA .,gave th 64c -4* (from du. Me'CO)'!
hC Q nil
to
1 U dil. HCI and P Ili (2 .) in jity xylent an 1,6 g. pzwd. 11 boiled 8
14.611
hr% d Glid
Vrartn NAOII; Purifi byaddrs,-ofNH,0IItoIt,sjn,jn .,an tiles ' fil(ered.andw ed with C~1,14, and extd.
14cl, it fit. 208-100. MPTI- with 207o HCI cave the H67 with hoillrig HtO yie:dcd I g. crude (0.3 X. pure) :,5-djerc-6.
PhenY!I~Yfifflidixe (11:), while the mother liquor gave UAS c,
jail, M. 108-2m. (from MOH), while refluxing I hr. with
Ac,O gave the N-Ac deyir. (11). m. The Tatttr mrgentyl ether, m. 196-2-30% insol. in HCI, sot. In alkalies,
treated with hot'ale. KOH gave on cooling a ppt. of the K thus Indicating reatir enalitaum e the 010 Eccup. The
enotate, which with dil. HC1 gave thn origirtal Ia. Hydta, ether refl=ed 5 h". ivith AeOR-HBr C&ve the arillituil U1.
teuation of I o-.er C-Pd La MOH Sve a carkpd. C,jIj,NgO, lit In - MOH W-ated with concd. a4. KOH, and The
'M'14GI-S' (from MOAc), also formed on similar hydrorerla- soln. dild. with tnucli 1W and acidified with coned. HCI,.
th"i of BsWC1j'jVHC0jVffAe (1b), and unchanged after yielded after several lirs, 1b, deemp.2300- (frota MeOH),
prolonged boiling with 220cy.; HCl or 200% KOH; itwAstither with d-CiTUNHOt it favv a
or P4Cffi)jNf1CQ1V1f9. I juittoraline, m. 268-71, . 1b with U104 In aq. cl:oxane CAVe IF
dissolved !a warta 571, NaOH, then cooled, gave the yelkw A*ntoi-s. to. 218-21' , and BxOU Cf. -C.A. 48, Mal
-- G-. M-. x0ho
"R,
B~

(361 R,
OL
p
-The
Fodor and Ow- sray (U 1 Htwst~.
Soc. IM, 234t-4; d. C .48, MWA.-~E=
(1) Waa mead
auu. ~d 25 - .9299 lyi,
W-Y."i0froxy grapdws (11). M. llv.w (Ha Olt. M;!
arA(
11930; Ust saft. tn. W7, itcem -)-travk &-d
TUls hydrdysis
lmffkd oy%rdnong 15 luv. *fth 109o1 HBr or 10% TH3
or 2 h". BaJOH)c. The dibea=te of 11. tn. 268",!
coulA net be re"ved by use of +mmv416UM-7.44:1-hidnixy.
SIN PA4I~ for plalyull-
1101OUSSHAV (11), ISM WMIR-Cille (11t). iv%jj. Pte.
vItatity reportmi MACUOIB urv cmplcoycd III "ffiviux tit them!
struclurtic It itatt Ill tire kuowii to Ix iv-rvN&uwcrs wtd
hitemal ether witen irtnaM with IllSot or soell mi.1 subse-
quently-A-itil klk., it 6:v4'UDIc-(l Olat the two (31tgroupstare,
clA to euch fitlivr anWand to N. A mechauldin
"
for the etheriflavlon macdon mi vi-t-11 as I& tromibl. t' to
rigarous proof of the propwd itructurcs. D. It

0
'19 MUM&
V,;
'ID ~-Evwcnce is Prvacntcd to show.
~thnt,TV6,fxmctIOOal JMUPS'at C-2 and Ma of Me 2-=dao--
ther In
A0.14M-CORT32 1 (Cjf4N),.are ocsir each 6
space-. This requires that these groups be bound to equa-
p~itions in &2-C-1 conformation. The evidence for
lut" of I dzanges on standing,la
Iles in the fact that
r, wto -80.6, the rate d-401
!s a misration Of an Ac group Irom
viiih pli, :.This tudicati
Acetyl.
C4 OH to C-2 Nil , yitldft Me 2-amloo-2,4,6-tri
0. p'. ~Itxcv~yrauoc ZU), . ..j. Imn. to be intramol.
and Ki", C.A. 44. 2511d). The prmnce of 11 In
-'jthiAei6ru1At6ry soln. (M) is shown by treating the t
-Th, eldin
iThh NCO; C the 3-A? phtnytcarbamate of 11, m.
(AtetCO).- The acyl migration Is readily
4"'b, -a"d,dial HC1 In M~CO to M, LHCJ. m. 233'
Aigure
i$.WbWed M.Weu as physical Zell-
'for ia~ following compols.: [c=pd.,--p.,aadjajV
vtol. EtUmino-3.4.6-triacetyl-0-0 lu Mu
joavekit
134* S' (MeOH), IVJVBr. 27 * y
r7l
Stew); &I ( at.
A. -S?f;
Ol'-flir, 7.8.
IA's 'It.;

AID F - 267
Subject USSR/Chemistry
Card 1/1
Author : Fodor., G. (Seged, Hungary)
Title : Stereochemistry of the tropane alkaloids.
Periodical : Usp. khim. 23, No. 2, 264-272, 1954
Abstract The structure of some tropane alkaloids is reviewed.
22 references (6 Russian): 1906-1952.
Institution : None
Submitted : No date

WON
Aplihitwilit wid XL Sljt,~la propitation
I, I
1,4 11 V, 410--diiji;1 3-ocla, ecanedio ;f. 1,
an,
""1l. RI-911MMMI-f Kill 611111310-1111SO4~lrivlt
(3 firs 1 fit 512.45 g,
m. o4! vmtwd with ml 1'. 01. wixt. k,-Pt 11
'fal" oovi r'k,411 t,*I,lp, *,It lilsioltl), thin ~~,lrtlltlt
Llovly ist r..:.o to 75-8u*1 (5 alld a rAn. Of tll.! r"I'lu.
fit UIR) in). pvtr. ttlitr lit -IS' ivaskd with three ILD-tid.
liewtioni W ice 11,0. Atterri~tul dbati- (it 0,01 mitt,) of
7
,fill gia, dtiot VURSO.) and C trcdtt(l, crti,f,! C141111CHAr-
COUT (11) c-tu6cd deenitipit. It (515.2 g.) wait addW (3.6-4
firs.) to W-17 Fr. N,C]ICO.-Ilt (111) ttod the riflyl
Uept over-
4-5 brit.), friviog CIA g; crude Ct4fljoCl!I!rCOC(;Nj)ME;t
IV). lit. -M-152', crystd. from 14011, m. A8-9' 'rude IV In
WO MI. ale. trvlkted with 36.6 (sk) till, 8.0'si X, t1a
1
(0.0 inoles) wlE3 hydrogenated with 40 g. 11.1% Pd-C pre-
reduced ia 5W mi. ale,. coned. '/a. and chilled, giving 77.5 W.
t furthrx concu. gave an addid. 32.3 g. Tro crystits.
= EtOAc to /do Ent.) rave ot,-CuHjtCOCH~NHj)-
MEt (V) IA salt, in. 114-100 (from Me.); V Hjjr. m.
111-12.6*. IV' Its,hexane with Pd-C was hydrogenated to
Et 2,"IpentadvcyIdihyJru,4j,& iiynsNedksrbox*te (VU~
V.HHr(W`i4S.)&udO.10ji.NaOAc
In 16 "0. 140 treated to ml I ' 04 A 0 gave Vt.
C, till
A mixt, of 27 mi. ActO. 35 g, W. VAICI, and
(M nil. Me0IIJtAci% 5 hti,. In the (kirk, buffed &r10 Mill..
filtered hot, it ... 1 0- qltrftte 6illed, pye 02.2 It. ciEude DL-
~,-Pt (VII), ftk., CrMA. from
tts

ml. hexana *.Idcd 83 g., m. 71-3*. 11 M crudc 0
-THCl pvc 7.4.5% cr"e W. in. 69-7 1 Ii ",'-5nltrc-
hcnylhyclr*=e m 105IS-7' (from hlo-111". '14' 3 9.
T311, I,, old NIcO' It cont;r. 6 drojn;!W~~, KOH was
I
added (W20') 7.54 a. IVAICI Iti 21k) mi. utti. Mcolf, and
the mixt. ttcatod after 12 tits, ut 20'. wiCh -110 mt. 1-110 und
extd. with rjvc! 5r)-:nl. por6ins of 1:W; ttn "lez-O.-acied
ext. gave (atli-101) with dry 11C1 4.76 g, crude (m. 110-11')
threo. and rrythro-ract:%ri-tto of
C')~Rt (Vill) lJC1 :Wt, in. 11-4-20' (from '::tOAc), Stint-
-turfy. V11 witli NaIW4 yivided r)t% A%At duj~. (11X) if
V111, rn. F~9-901 m.n MoAc). '011-111-1 ~vlth Ac~()-
AgOAc gave IX. YX heated with Ac,0.1, IOAc nve t~m
0,N-di-Ac deriv. of Vill, Fit. 93-5-0-5* 1(rota
A suspenslono! 1.9g. V111.11C) N30 nil, PtIO wa-~Ixlmken
10 Fula, with a Soln, of 50 mi. 6% NviOilc and 5 nil. N
NuOll; tho M,O salm, of Vill wvi w-t3he,l with 10 ml.
11,0, dricil (Mg50j). nsid Vic Vill In GO mL llt,O treated
Nvith 0,55 g. LUM, in 2.3 111L Ft'O and, ata 13 lim, i~ith 5
Ird. 17toke and 10 oil, Uto, giving t.2i) 1;. wixy ImMuct,
which, H M,O. yicl&!) vdth (try HQ) 1:ie rarematc-i of
(X) lfc~ Salt (0.75 g.),
FIT. 2,1jQ-4 (from fi.'WAO~ X.IICI ivith diclo-AgOAc gave
Otriv. 'Al) M X, n 1IS-21' (from
UtOAc). IX mitfit 1,001, (,,jui~imhr ?At and N-TABIL)
yielded 97.570 ertole X1, i0lick iv:,-, cryl :d. from NIECN.
1SOBrj (2-3.54 g.) wj1q;1'Mcj (2.5 ljr~.) to.5-2 z, I at 75', the
q,~) 1,
mixt. heated 4 livi. at . trt-mul witti 20 nll. drN, C.U..
al"I the C4114 reffloveo in vlzcuc Ivith -;Ile mcess'solir,
IMF WMMWM~ I I

A '-T 11 ~7-
added (10-16') to 45,11 g~ III in 40 nil. pett' tihef, ind the f
nilit. kcpt I day at 0' ;%nil 2 day3 at 216. tht" tmktcd with
10.7 V. pyritfint in- 5q M. PCO, Other; the I-cArbctf.'c3Y.Y-
metbylpyridijahtni brcmildc (41.3 g.) which pptd. in. 1t2-
15' (from ClIC11). The filtrate, wa5bcd with Uwe 30-m1.
or H30 II 111'~t 30-m1. portkffs of 10% 11cl, and
We 3a1. port1cmis of N KOH, dried (MgSOJ, coucd. in
p
Mew). and the residue (65.5 g.) crystd. atO'and drk-d on a
cold clad plate gave 44.S~&CtAsCOCIf&COi8t (KM), M.
I
35-8, from ritoll).." -hydrogenated In HBr-EtOll
gave V.1111r, Georce L. Sutherland-4

~LJ
-
r
V
S IV.
5
11
1
"
171
IM 1
'-
-
t
W
&
(
7
e is
ft
r. on
1,
t
.1
.
. K
OD
6
1
1
Whm
J--
(11niv, &exed, Hung.). - cltlw===j7v
inn
114376~'rhd I
A
48
C
.
.
,
t comilue Is definitOy doW. U
30-twmayloxytropade.
'
I,* fuldA dur
!
imllt -47.301 Ing 15
a
v
urmf
min to Swr YkIding n" W& fig up The :d4
. 1
M =2
(
8 "
0*4
c 2.11, HJO) llne buse (1), ni. 76~8% maldif ins 24012 t
50
0*
24*
T -67
i
d
8
0
d
2
)
-
.
-0
ecompiri.
. 2
n in.
an
1
sp
(
(4 2.101, MOM: G&-AcO arialog-&riv, Rd, M. m
A'
*
1
t
7
11
1 d
eft no
"
2.00
Mmimpri.). Ickiv -59
(c
.
%.
th Mtl at roctu Wisp. I acEtnt(-H d4votwit in CjH#
wi
d
was heated on a stwm tiath 1cw 4 hm, yfttdfng uUm4de
:,-Z' -cf- the (aftwal..Jda or
Staft fig
fill (U), M.-M a
*
'
0
"-) . is Pf
Z4C-7
(d&vntr
(c I.BW. f1f) jelcrate, m.
or beg
rh
ti
2 his
tl
th t
b
f
C
"
t
.
it
mn
k
e$
don a S
v
.
as
s
I ki the abswce of moisture to IMI ot ftfluxill I c1
RtOll wnflic. XaJICO# for 10 lits. It is not teted
Ran NI&tFM atrimi.atO01 for 5hn,, buton tmatrawtvii i
.9 HO In a "ltd tube at 12P LHCI Is obtabied to"
47% Iteld. A Ooln. of MOM in WCH and U was ritatiled

(c 2.107, Rt 011), prob4blya mixt. tit 2 immucrs of the nwoo.
Pt ethers of 4 ef'onfilol. Reaction of It with Naoll give a.
rubtt.olC~ -t,inicr%of2-hydmxy-3-tropattol. t.HC[Inl
MeOH was treated with NaMle. hydrogenated with Pd-C:
at 15", yielding
(98%), m. 20"1 (dectimpti.), a]-j? -30.5- (c 2.787.
114) (ftee base, m. W". (*116' -6814 (c 2A64, R(OH).
.30-AcO analog dttiv., oil; 30-AcO annIog-1111r, m. M3-4'4'
-39' (c ZM8. EtOtl); N-methindide, tn. 300
ttlecompa.). 2.5" ~c 2.002, U01. To a soln. of
rtdistd. UrCK in CgH% is added 2$-methYt_V-acetoxytro-
rile at 60" and kept at that temp. for a hrs., coned. yield-:
and an oilb which
ng C
it d with NoOH at 100' and working up gave-'
s
er y rolysis
(IV). m. 10"", (aIV -57,0.
2.002. MOH) (H deriv., m. 2W-6* Id,!- n m1V
-43.50 (C 2.182. H30), - N-Hz dtdv.,
.
192" (c 2.14, dlax"e)]. IV id PhCl, satd. with M
fxted With "IttubmitMehyde. buted In oil bith to;
420 PhCldigtd dried with bfgWo and put back Into re"-
tion 9W, heatedl; 3 ha. at 100% PbCl distd., and the red- I
due etystd. ykldtul
of IV, m..77-90, (a 3Z6 (c 24M. CJ16), which on (mt-

ment with tIC1 In ELOR gave back FV. Ox!Lti~~ a iii
*ith (M-MW and C I fit anotie gave 20-mx!hy1-3-
Tic, n
trovaliGne, tj* 125-W, (a V (c 2AII, abs. EtOll)
gait, in. 200-1*. [a) V - 12-V (-: 2.0W, Hift (mime
H
(C 2,W5, abl- RtOMl- V
n HO broutht was heated on a st-um bath and
then treated- witha solo.' of Vittle ack! itt 06% RtOH,
yielding Do conch, zd-MWAy"4rQPaXV" Pkrak, iii~. 213-
W, from which the parent coinfid., tn. 1WV, [Ulu
obtalned. T=tment of 2a-
was
hydrox ethyl-3"opnol-HCJ with SOCII for 15 min. at
V, rlj~ - - I I, - - -1 .~ .; i
Iding 2ar-ck1arvmdAy"=P4%4-HC3, in. 263-41
(d!nm ii.), fall? 56.51 l(ree 954*, IRIV
7 ec -9. M011); metbM)cnn. 2,,.
67.7* 2.074, al: de-
compn.), [a]u 4 - V e 2,W2, IfO)J. wW on rciluction
for 5
Aut 90 atm. premra and 90
with Rancy Nj in M,
tirs. gave la-mclkyWO-7ard-110, m. 281-2' (decoottin.).
lfrea base, V M51 (e 2-
-bs-.,RtOH)-, - methiodide, in. 294'. 1,awlif TP (c 2.004,
Rf
u.0); acetntc-lint, tn. 10240. tall.0 49.3* (c 1.943, aW.
M0101. Vlon refluxing tn C.Hs for 4 firs. k11JVL 1111thlingCd
V1. When was treated with
HrCN., iV-cy4notor-Im-toethyi,lp-a4regovylropan,-, in. 79 -81'.
1. 600 As. MOM was r4)(idn' A. which on Ify-
Y,31; wit I rI. Nik6l( at 1(W for 121 lip'. ~,416P gff4tv-
d
ftribi'la-IrONO-1 (VU). M 12-14% 2013.

tmpf 1.1 with CtOl in gl;lvill 110AC pv(~
I
f4inme JIM deriv, ill. 191-21, I"Hy (C 0.430, )1,,
011me, in , MIA* foli! -38 " (C LOW, alm. Itle
The N-Bz derivs. 4 IV nad V11 ~ch und"wmt I mic
tkni when tfrated svith 2Ar 1ICI In dimine to gi~;Ct~ 0 IM
:ester salt, tit. 2700 (dem"nt"t.), [OM -47V (t 0.
Ifto), and m. W, ~dmomvn-). I&IV 53.4* (c 1. Iflo 1, ft
also gave acyl Migration 11, H
dimmic W yidd O-lxnroj,hn-ecrnIne-I1C4 m. 1.23-
420 (11.0). N-Cyananarewafist in glacial UC
was tmted with coned. HES04 far 4 J:n., at romn
Ft.0 added and the soVA U-c-Ated vOth aq. 2N K41A
yield m. 179-60'. faIV --27
(M*OH), which was reacted with NaOSfc In MPOH
- 15* for 94 'in. to yield theAfeciW, m. 212% [*IV -.93
707
qhfeOH), and thetydi4 fireide M. 198'. I(XIV -1.
diumthutlan the omfiltirstd= of the fiapd.
dMolulds CCU omirk ftmetlatts atftche4 to
rolifte ft. - "Godor, ~ ~Wlh~. and 1. Vinere
MI-13.-A new rmethrA W es 'shO Me cantimitat!
(if mlrjno KICS. with a teftLlry N atu. 11 91tileg I loid
h. .1 - Ij
-kad dt-1,114, YAMYtz-an 14-

t

i
i

M~'

ftliMed by reactim *111, llmcogt t1le salts of the
currorpDridiag tactanev of the N-carboxymetlayl deriv., in-
Thesyn(O)F
osItirm
of these
r
tha
f
d
11 d1
C
R
1
4
r
qso
l
oups
ore provt
.
vv
m
g
*
4
Sind "died with TV Came the 144,qe of N-c0rkxYq1114Y1.
01ciatum Wih US*, whict. on shaking with aq.
of rh*xyPndA*sdxe. m. 2661
d
Pa.), reconverted to the lattone with Ill. Scopol.
i(
jam(ne-FIBrAlItO In RIO tteated %ith KaHC(IiI, extd. "ith
MIC161 and dried ever MSSO4. y(eitted amacphoin scopol-
amiae. which on tmbnent with IV pve Ae4rNx"dky1-
Ice , Mimiksm iodAk. M. 1551. which on touxfng with 10%
I cave V. M with IV save the 441e Of
&Y-ca&xy.
M.9m, (decon1pri.), Which
'
t 21th A
t
t
i
A N
W

na
m
(
men
-tartoxy-
a
n&
N Vvn a
ll
(decmpn.). I
to

with IV
ova JV-"f64&xr%e; Ado Asia"
Wi4. m. 2041.
sad a f
t mctlm In 2"6 which on ticatment with Aj,0
'
252"
h
tl
b
hi
e
e
m.
gave
e,
ch on treatment with HE
. w
oxWltcd wito
the tactonq did
C. ftrc4m~
w

S m3st rphiringollpides, .101, Cuirclation of X

Mr
Corgiwis), ci-C-4 . 49,
(1), ill Fol fill. ull,~ clic)" %va-4,
11 UN
Stilit 1111V 11A) 'Aai Alcemst,4, Vic hLA Mv-ict~atttr with:
V;4Q:) rtsilble (3. 1 K.), vrv~td. fillill $A-tr. Obvir. X;lvc 0.42
X. lll~r6ticp(!W (11). Ill. `,1 3", Tht por.uther :,0111. gi%V(
a miidtm yid-liur, 0.7 it~ mys 2.-Williff"101% llyl,
-loltarom-, tn. 106-V (fwln L'toll). Oamlll.y,i~ 411 () g.l.
(cmitg. fat-%ol- nuittirbl) rt%c a pirolluct WlIkAt itritted ili
U) mL ak. with 4A lid, 2N NaOll ami -3.7 g. SActixA6o,
thilirl4littill (411016le lit '4-l lilt. ak. WhiCil r~avv 2.5 tf, of (!it!
-Wi. of If. fit. 1384 (froit, molo. 'rile, orotlAY41 .
pliml(Ici w;ts titcukmized with C and evaixt. in j%jetop to Civil
a thisia Brill. dioxancillixed With8lill. Vtsl ;
it ;M 6 nil. G,%1 HO lit olioxanc. and sitalmit A-5 days lit a 1ximli
tulbr, gave '21.3iij g. crode prodtict, which iii titrn gave 0.14:1

1,11,t* ~T,2* (i 0-5541, IjkO),_ 1;%-Apg. the C ,It Cl

ti
IfOrt A -9. laxo1thed I 9jvL- an oil Which vrt-i lifl;f~lmd N) alibi.
at FO-1111" Ovthl x0th 5f) till, :Wk HA. livalm. A life
Aq. sMIS. save 1.5 g. oil; 04- on Sliflifillic I Wevia: ia :!5 fill,
110, votteg., aidding Me. allst c*J11t. cyl%pi., ult;i ~ttystg.
the reAktue trot" 10 lul. 111C. pvc OAM it. Ill. lim-pil. all
the fill(cate and I exAns. of the m0ite (QA4 t.) with nk.
gave srdue. 111 (0.28 g.) ill 15 fail. H,0 was. thAUn !I davit
with It aud 0.4 C. Pd-C (12% R10), thie, mmhincd
wi4shlop evatlait. in r4ecto, aml lite mHuc tucatol' witll
IIAO-N-all. toqt m NOR Swat EtOll-CGO to cive 0-A2 St.
10
(IV). in. D)7-8'
(dtmmpn.), IoIV 22.5* (C 0.4, 1W). IV (0.11 g.) ill 16 nit. at
tj hy,4roCeSa;.ttd 4 weeks with 0.5 g. Pd-C, the ftjtm~i, rijij
witshing-i ev3lxi. ix mcna, and th4j zciidue. Laipitil, fremi
MeOlf-960, c3ve 0.03S g. hycroteop;c
itmim-l 1,4-tauumtriol-l(Cl (V), 202.4", 1,7"Is
(e O-V-4. 11,0). IV could also be by-druxenzated with
A

Pot,
I mxv., t cluct utill I lye L~
f ~un -Ilyl NY- -1 t%-( Cto P-11 I (VII
01 m
live 1=11HA (A Mittel at ablicr 4 A
(C A 3
by-T"1%I -t putRilyt 'I-
uk t
cquc c
fleft"m 104
-IV' c .3. IM Ali uq, %;m1wi 1 4.1
OrIttril ith IQ oll, tv N3011 pvt: 0.7
twimic (VI m IF'!$-f6a
(Irmn UI INCIII-Imtr. eilmr), Heating (1co-V) 2-plienyl-
lirmn-11CI alto pvc
till"mm nptically isiactive and cotthl not Im- hydrG.
Oftateti st 101) tom. with Raney M. VI (2:5 g.) (11. Hall
1l.,1#c,e0.)I% 160ml-11,0with ISS. Hativy
12 It". at 90' an't 120,.Itni.. 0.1 g, h1g W'der adtived, hydro.
grmfkm CmAtinutcl 4 firs. at 100-4, illid V~l atm. (When,
tht, Vchling test ims net.). the comblutit filtrate and wailt.,
i" cd. im r4cue and erdixi. With a1c. CJf., and tile
~1)714-, fron, Affoll-Eto gave
(Inaluing), jaj~" , 1.67' (c 3, 11~0). IX is thu nnti . c of V.
SimEr mdoctkm of 2-5 x. of tile z)-L~onw of V (11. and
P., Itc. Cit.) gave 11A g. V, jai! -I J93, (c 0.8. 11,0), m-1
MV (ticcempn.), whic-li did not dcrwe." Me M.P. of V fr("Ti
L That sphiogwim is
44r4fts-octaderene. 11. "NuthcrUnd
i~j

V
W'ciltit (Uiliv- Sj
011 o( ill,: Coll.
-file fo 1!o'k ill;
(11, Oc(r.-I
o-mi,
Ile'v tilo
fold tj!.::
to
Me ,,.at fill,
In, till
I vl !t T i~
ll'i Tv;_

--hcolf-M)IM.- 0 ter Pul-C at atm pressure gave MJ.5

hesis of chloramphenicol._ G. FwMc 1. TMh- F.
gyn t,, rp-
H 4 14 ,
WIIOCII-Jil biLlU
'
'
*
i,ovacs,,,tndj.-KTrmniw.-bzL,get. ting.). i9mij.A.d. 1-3
40
(ftnut EtOil), which yieldcd tile frec base, lit. 8-
.
-51; BUILe
S.S.S.R., Oldel. Kkini. Nank 1955, 441
Electrolytic tt,du(tion cf I iti 100 tell. AcOlf and 200 nil.
,Icad. 3cj. U.S.S.R. Div. Chem. Sci. 1955, 391-9(Engl.
96% Etoff witfh.l~ Hig-pool tle-cti-mle ami 2050 EM
!rari~Ilitinn)-, cf. Fedor, eta[., C.A. 44.7273g.-PhC11:CII- lyte In it pt!mus clip Lit 0.07 Rinp./-q. cai. anti 4-1-5', tile
CIf7OAe (01) g.) in 450 ml. PhMe added to 400 g. NaNO, catholyte Milk, lit 'lified with ITO, V-,tV,! ill :1 fift%, froill 14
irt --0 fill. 11.0 in a dark vessel, the %tirred trAtit. trzated g. 1. 2.4 g, W * I

7 I;r,*. at 0' with IA 1. 20% IllSO, with occasional bubbling
169--70' (ftuni AcOlf). 11 5iruilarty treated in a1c. I Lit
16
,F C0,to break the Itiam, and tlie MePh layer fillered gave 35-7' gave 28~`, 'Wrte product. M. 1W. PIICII(010~,
Ole crudc product. which, a-wilied witli.EtOli and EtOII- CII(NH,)C1I,a1T 66.7 if.) in 100 ml. ITIO and '-W mi.
]"t%O, - ykid"i So - g, - t)l:~erythio-phcl-l(,VO)CII(Nos)CH, MOAc treated With airlilig in .10 min. witILOO nil. -40%,
.0lic, Lit. 124*,- "liscoloring after several weeks' storage. NaOll at 30", with the pH kept at 6-8, the aq. phase cxtd,
This (r,115 g.) treated with stirring in 224 lid. AcO at 25-0' with MOAc. tb~ -!Drubitied org. saltis. evapd.. arld tile Mi.
over -10 inin. under CO, with 24 g. coned. 11,504 and 72 nil. duc_treated irRh Etoji-TICI gave 50-5% DL-Ihrc~
Ac_O, stirred 50 min. longer, dild. with 1 1. ice water, and Phcll(oll)cll("Vlii3)(YWAC:JIC-', M. :17-4', which with
k,~pt :3-4 cl-,-.ys in a refrigerator gave 69% jDL-threo-PhCH- K2COl gave theft!e L-ar% ni. 126-8*, identified as ix-threo-
(0Jl;)C-11(NO2)CJ1,OAc (1), ni. 72' (from EtOli). Ml" PhC11(OH)C1f(NiYAc)C11.-011- Cl!CIlCO=Nfe iwstiad (4
ClJMj) ill lb-z above re-action sinfibrly Irave, after treat- EtOAL: lit the above gave 64.M` T)L-4hrf0-PhCR((hCCf[-
of dic proetict with Na-COs anti N44OAc, 0~)C11(JVJ1i)(-'1j:0-FLH(7, nt. 'llie latter(M.715

DL-tPfeO-PIICII(O-CCPCI:)Cli(iVGI)CII&OAc (11). ru.
-M/~
g.) treated With 1.5 ML H;O alla 139) 1,~-ll lit
ml. EtOAc, tl
(c,,Llde), m. S2* (fm- EtOtl). 1 (54 ff.) in 960 all. 255* with 3.45 g. X,M, stirred 5 min.. and eNtd. with
Ml%CO trcatckl oycr 10 miti. with 1.150 1. N MCI, Olen re- Ht.OAe gave 7-8O!, I)L-)h-o-PhC74(OH)CMNIIC-IjrlrCl,)
:L5 hr,., micd.. treated with 130 g. NallcOl. C11,011 (111A ki ,'t4-5' (frout 50c,1,) M011), which stintil
exid. w1d, r-i-0, and the ext. shaken with KIIS04 giive i0th pyridine-Ac,,I) 0.5 hr. at 100% yirld"l ~~a PL-threrl-
OS.511,' 121. ~&1.5* IIACII(Olc)Ctz(jt7tcOCIICI~)CE~oic (11111), Lit. 113-6,
(frr.mT-'.t.0-pctr.ctIicr). llydrogetiatian of I in AcOll over (framGO'7cXtOIIj-, 131A kept 15 nlin. at 70' with Ac~O gave
P(i-cat "Ontra. gave 4017, tiL-Ihreo-PhCll(i)li)Clf(jVll,lc)- 72% i)whycc-Pli,.'11(01[)CH(NIIL'GCIIC'I,)CIIO.4c (IV),
Cj:~.O,c (111). tri. !6.9-9* (cf. U.& 2,4,1rj,KS5, C.A. 45, m. IW-l~ (Irani GtCFAc-pctr. ether), which with abs. Btc1-
which (I g.), 1,ept 2.4 firs. with 5 nil, quitioline and
- LtOIT-110 at 0' ji4d,!d in 24 hm. 7-11/0 xlL-t1lrczi-PnCjj-
.4c)-
.1.6 7. Ac-.0, gave 1.1 g. rjL4hreo-lhcll(o,4c)cli(911 (IVA). m. Ils-7' (from,
rt'!;OH, in. 70v-811*. Ill refluxed 2 hr's, with 5% IICI gave E10II-Vt-0). IV (3.2 g.) in 10 lial, dioxiiiiie tiLutud with 5
fit. 192 nil. dioicaur. cuniti; OAJ4 x. JINOj atO'aud krji(:LcvvraI days
(cf. U-S. 2.51%,116. C~1. 4S, 17W). 1 hydrogenated in Lit 0* gave 7.-,.5LL HNO, audej (LYB) of IVA,

\/syntherjs of 6-tropeu4w-ol' a Euggested Intermediate for

,
JFIK 101r* j VIM. I Kocztjr. and I ~ Viiicze
Scoplamine.
~,
Chemistryt
C
(lust. of Org. Z -7., eii'llulig')
V
.195s, 121W- I,Tbc tjtle wv's prrpd.- via the w4r.
tions: w~ii oitivi,ried it) lv~ t%\
phenylurethazi, m. 127--Q',- which mut hydrugeral ~ I to
I was aect ylated and dLqttl. in nu tic, result ing in the revemd

T"
nf urethan fonwiliom, yielding (zh),la-acetiy -63.11 ydr(%7
trollatle (H), In. Innics) was tr--
11117le wiyl chl'Wide to give the
clt;tYtd by o4lidine nt IAO' ist c. N utut. in a scaled lube itito
G-trolven,t-yi nertate (111), 1~ M*. Wrrnprn-.%.-A lpicrute.
m. 278* (decompn.)j ivas prcpd. by the Kittiz hydrolysis of
WO

17"p,

IL
stadlis In the jyfijqj,~~e W.1g), suspended in 11. C.5N NaOI I, extd 3 times with I I
*A'4m #zaa'
Olyal at naturat hincisda jCf,;, ether, the solid residue flout the evilm. of the combined
G". Fodor. find D
Bin v da
106jig. ether exts, dbsolvcd in UO ml. dry C.116N. heated at 0*~
W
N94; k&IC-A - 49. Mie- with 120 mi. At-30, and 6ited 15 ruin. yie'aled. afler s1A(W-_
To collect a 11trMtUT, ?
nk attd Diebold. a 1119 at clay [it the cold, 29,,; C. tri-Ac dtfiv, (11) cf 1. 1 Afr._~
23 4278' N1
n t4
:d C 4% .11? -9.7* (c LI, CIICI,). Alk, hydrolysis it
o! vhi
(1) and its pye crude 1. m. W78', irhich (1.1 g.) was reacrilyInteil to
bivestis ted ~e afate of I C ykId 1.1 g. U. identical v,ith the preceding .mmp;e. Thus.
Irtl is
th Re hy~
no Walden Inversion had occurred doring the. pirim, of U
5!1 C~ C~
a fit to CAtirr. C '-from Upides by their acid hydrolysis, foltjATd by the alk~'
_ri
hydrolysis of U (cf. je:lny and Grob, C.A. A 851'6'y~
Partial alk. hydrolysis c-.1 6.4 C. It in 200 ml. McOll by
letting it st4nd 12 hts. at 13* with 40 mi. N KOII fit MeOU.-:
evapg. the mixt. to 100-211 mi. nt M)*, adding 200 ml. Ill0i
ancl extg. with ether yi6led from the ether ext. 3 g. N-Ac
deriv. (111) of 1. in. 60.5', [r]'V -5.5*. (c 2. CIICla);
mixed m.p. with the dih idto dtriv. of 111. 62-111*. The
mother liquor front the Irt-lin. of pure 11 fre-A frout the
-solvent ilt picun and tht "sidue di--snived in CHO, and
neutralized gave an oil, li)~mj 170-%.' (bath temp.) [all?
-0' (c 2. CIICIA wobably C,&TfvClI.CIICH~0R )-
CH(MIR)CILOW(R - R* -, Ar, R' - Me). 111.3 9.)
Imn tht alk. hydrolysis 0 2 j. 11 in 10 mi. dr~. C&TI&IN
tMated with 4 g. p-ONl:&II4C0CJ, heated 15 unit. oil a
steam bath, allowed to witud I day at room temp.. 20 Mi.
HsO added. and the mixt. extd. with ClIC4 yielded 1.1-1
g. triq-(k-nItrobeazoyI) di-riv. (IV) of 1, in. 136-0 Morn
-907o McCO.IfsO). SinAir tr!atnient of 2 g. d1hydro.-
sidlingmint (V) pvc 25 g. tris4p-nitrobcnzny!) deriv.
(VI) of V, T. 14"' (frim ab3, ELOH); mixed m.p. with
IV, I3&A2 . Alk. hydmlysls of VI give the N-p-0~1;-
11) of It, in. 124-8' (from dil. EtOH).
Cj14CO deriv. (Va
The stability and crystu. properties of IV, VI, and VII
(rvfr R

were not it and on
It 141Y10101.8c OR
d f5jrrb'al it
.
-use
1.5 brs.. at room PP' 5
=g tNr=dUe 56 Wuridigalod 1.-
in vocgio
elici C. ZZ by heating 8 hrs. at 120,.30* in a qW,4i tube With
t
,
-11t0, and ~ooffngAn ke ylelded-4 g.1_HxO4u&tl- 0 -0 10 031. If.0 iPvt a tri-Ac deriv of an 2.nino tctraol. but
MWk iilditt:.. failed
pWi;j~, becatse of the migration
sepd, by petr. ether into (1) 0.0 S. Pelf. ether-sol. nil
acid, in. and mixed m p. 51-12' fS-bensyliwthbironiuld salt
*
1
d (2 ,
of aa Ac group to that no vkinal
Oll groups remained. X.
OPM of t4trard)
-Chila fifirbatle ketones
1
2), an
(cf. Donleavy, C.A. 30, 510
)
in. 1318
t
which reduced FtIlling
h
d
id
(M) .
.
M
T. 1W. 5W-A(ln rrm~mKllittlish ounmary).-
e
e
Acolf-sol. myristit
,
y
11-dinitrophenythydruotte (X)
2
soln
and yielded 0
7 g iAS a ttep toward Complete syn:fiesis of sphinrosine. the
.
.
.
,
'X . m. 104-5' (from HtOlf). Th a b er sepd. from
of y
a: of the
eva
z alie
l key .. ft-culinclIXUAC 11), was Pt -ifter l1rc-
UM, e -

pt-,I. on model con pot,, R-CiA Ir (484.8 c.).
X
r
n., a
p
Vill d6o reduced Fthling 5o
solvent. the residual (2.28 g.) sirup was z-tytatedtoll.52 c. warmed 7 hirs. on a stcam hath will, 306.7 g. pOC4 accord.
1
I
to PI!
d D

AcQCll,CH(NllAr,)Cjf(OAc)CHO, noncrYSC but Chl"' MnCr an
ft
utch (C.,-~. Z3.
417). gave 646 Z.
-de CaH.OPOsHs (11)
734:2' (sam
m
std
lc recr
o
f
acte-,ized by its compd- with 2 4-(O,,%%CtHsNHNHt,
Entylblv tile omzone of AcOCflScii(N11AL-)COCHO. in. .
.
r
m
,
p
y
CHOO. WSW. and redWa. af:!Yj e. 11 in tucuo gave the
f
p
175~-S' (deCOMPtI., softeuing at 160*).- AW (CM the CIOM- -_
um Of the Preced'U'F ozon"Y"is Prod-
N10thet li
ed a
bi ractions (C., b.p,. r,W): 120-5, 1,, 147-70- hu
__ 146-53*. 1.4424, 76. Ni IM-79, 1.4431 fftl)- 20,-LN 155-
'
n
q.
q
evapd. to drynen, ard the residue estd. with
ticti. acidified, 7
. 1.4445, (honolysis of Ill ticcordlig tr, Asinger and
Pdwtdt (C
571
A
38

ot abq. EtOll. was obtained 0-3 g. 8-414il-12-1A &~
buly'Clatt"t 11C7 ;alt. m. 218-220* 0.
tests
i .
.
,
) yielded 8.11 g. mixed acids, sepd. by
vvOurn ditto. into 0.6 1j. laurle, a 9)- Ms.*. and 5.1 C.
b
Myristic acid, in. 34-0', characlerlwd by tbeir S-bcnzyl--
n
jl,()l, whicl, fails to give ninhydr
t X
Similar 02:0noly,49 of I rave no bolatalk PWUcu 11-P
oti
l
h
o th
d tsothfurouluns salts, in. 140-l' &:d 139% mp. A zhift of
the doubt_- boad hul obviously otimried during the therinAl
s
r
a
g
The splitting Pit the double bond was attempte
tile epoxide' 6.1 t. 11 [it 12 ml. CHC4 trmted with 0.25 9-
in 51 01. 11CII, allowed to stand 2 dais at 0'. and
evapd. ils r"NO gave a yellow oil, whose ethcrfnsol. pot-Jon
~oxlde (n) of j3. tn. 134-601fam MeM),
-Mg-el

J; K
7,

a. of U.. Tile- -ilmd ~dre I-et'Itd (IV) w" VMPO,~
t
%
d
4 I-WiF 8
in

a
Vaitermau,
.
fMrT1 ceartling to
411"O'cCiAl M
V urWer N 4 hro
from
Z4
he atiti
R;O g
l
n3) b
(CA M Myers (CA. 44. 14mcii, I-nd Itli Acid Oloride (M)

*
.
.
.
.
,
y
c
'
* . with SOCI, it, the I.mal way. Treatment
If"
, &Ing 551 g. distillaiv (.W g. C,sffte
bi. ljo
to 1),w 360 male X1 with 0.1 stole VU as above yielded W170 crude and
COAH ai residue). Tile oily diltitlatt In 11. petr. ether (b. 59% pure 1. b, 150--40*, a)? 1.411M (stinicarbawne" m,
vraished with 3% NaOlf and then HtOH. dried.
ed 5 f
Altered
neutmUted
t
d
ith M
fl
r
i
t I W-12'. ruixtil in.p. witit ):, I M-20'). takEn J3 cvidence-
rea
e
w
L w
ux
s.,
re, re
i
.
,
fractinvialty dIstd.
und dried apin g-tive 448 g. crude IV for a traxs-tthylcuie configur ition h I tef. Fodoi and KL~*,
,
2:l6 g. pure IV. bit, 153-7'. %1.0 1.4416.
ia picuo.to yjcM C.A. 4,9, '=:!e), Ov,~,Iyxj:, of 1. rollowe,i by IfA QyMa-
and reduction of I by P'd-C
tion
aye FA)%
inyristle acid
_
,
Ozortulysis of 30 g. IV yk-lded tile ;_'XilteW C1416010 ,
, g
O
g t: IX both results being confirritatimm of the strw
-v
tvic
i
(25 g. crude), Ili. 113~5' (from EtOtf): 2,4-dinitritiphenyt- -
.
he attenipti:4 condmudion of I Ivith EtCO. In tile
JAnda, C.,4. 20.-302). IV pre-miat (if Naff (cf. Sohntay atiff Li Forge
C.44. 4Z

(22A g,) ill 50 ml. CSI tintl 14.4 int. AcCl in 20 tul. CS2 at .
,
121M) rive tinexpectedly 3-C,?lf,~, with pcrIjapS a SnLAII
treatt-d (biring 30 mill %vitil rapid Itirring %00, . :,,Ill. ,f :,,, ,,Cf,: C:jCOCj IICO,F:t; tills rv"tion will be

AlCh)i,1&AAh'Y III" ft,tihi ilivvitigated- X111 Preparation of tit.-Arro-2-,
7.*2.-- g: i-ily crt.Av C,MXIl:CIf3c (M. I. Stllay and F.
[,.Idy 7-95ro) intre VI. b-, DiaL-I P',id. J110-6:gin Eugli_ili); cf. C.A. 40
R624c.-
1". W "frAnt HIM)[. Tilk
Ow nwdi;id foli untdogs of VU .
Ill, lit, i i,iusly reported .I I itlivsk (C.A. 49, ~ifg)W (if If.
i

(VII, will, jjj-wf-AJ. m4ff chtfirklZItl preyhrasly
11t~
101 C,;l1"Cll(Oll1CIl(NI(Ac)C 1.011 (1) iii twAil
mt hy the
l
,
,
:i~;ed for Ili, of laid, Looms (Gilman und Neliun, wA: t-f tile lapp-KIingvint
im micti-i I.Inn. 247, 21A
1913S)l 'Iii I"t Fu~;,-d Clslf;i-
'
CA. 30. IM)511). As preliminary illodel exPts., 0.1 11101C t.'0,11
d %Vill) SOVII alli,rdill; to 11-1ktoll al-d &.1by
Irvate
VII. po-Ild. according to Cason (C.A. 411s 397g), in dry
i trvmcd with ice c(PAilig during 10 Iffilli with 0.1
11
C ,
C.A. 33. WWI), yielded X~,; pure C,,Il,,,COCI (111). bq-4
'
i
, ww
,
alit] the IllitiL
'
,COCI (Vill) In 1-10 Inj try Coll.
llwli: CJI 65.2--S.0
. Adding 5rj.2 g, AcCIj,lCU,Et in 4W rul. ether
-
'
1
,
.
W inf. 10"
ured onto '
C-ICAl to W
and itu
tIIV1cd I l1r
l -Irripwiv
to 9.,
41 g. litn"I. Nit in 4
W ad. etht: , stinitig, ti:,
.
V
.,
,
10
_,
; frojin tile C41fa laycr was cAltaitted 75%
ict-oild 11
S0
flux;jig 2addid. las., Ading ilropwiw P7.7r g. III I,) tli~~ ice-
.
2
4
COI.Ac, Ill. P-4, ..Sialilarl- cold Inixt.. nflujilir I lir.. mid jr,urilig it
Ito 150 IIIL 10%
-___1 - -
Irlafrawilt of Ctil,ICOCI in place of Vul Yielded 707g.
se"Itcarb-Mme tn. 121-2*.
1
4,
hc!x 2 g,oxi ~idtli enemn-Agetl theutie of
11
itt the Ocepri.

tic', y
cped frovit C6 ether lay" JI Al. (201,
175 iscontlid
and Mercklitig
A
41
V
a d. (C.A. 43. M7. Xv. Structwo
'
-
-
1

.
.
.-
,
-
C#lf4NjCI Ormn 2.07 9. P-OiNW1441174-Itt 10 mi.'.
t
1. X ss aod L
Lagaglyco4ldto. ~
. Ibid. 477-M
jurcsik
--A
I Th
(7P. Eu
Ii
in
h)
Ii
i
j

C;oled H.Oaddt4to,7.34 a, U In 12 mi. MOH and 0.46
t= s
.
nn.
m
ary. cominun
cat
pre
g
e 43
utlwtvvd s1ructural probt-cm (6, the 3 g3hingoglyeielts ( J

X.-Na In 15 mL EtOll an! the resulting emullf(M stirred 30'a _
Is Me Qutqtian of cz- or 041Ai;ge i4 the. gAictrw., Cerc-
vn.in~ at roorn tcinp, yiddcd from the tthtr cxt. LO C..,
-
10
91~D (IV) broil, kergs-In. and immu weiltser-arately hydruiyxW auid
.
,
in, I
( 101v valuct d'Ad. for the HI'M!,rawl. Sugirs, tagother- with
74-4' (from MOR). Ort hydrozotaiian (r.*r Pd-C In 2S __ Ehoic Ict, Ft "I.111. C
L-a I
--in -MM'"rififatft Alrit"~

FU
ether, 0.9,15 g, IV ab,"bed 220 ini, H (theoreticAl. V24 mi.) ~- .41nkage is therefore probAlt for all- This~_cotxluloa ila-
to yiel~j Inactive CuI1,,COCJ1(CO.1Et)N11&C1 M. M. and -ttiercaptoly sm, 'at' I
confirmed L-1 the slow (" hrl.) rite of
ndxcd m.p. 114-10* (from AcORW (yield not -given). .
.t
rwm temp. of, I (cf,_Leinieux, CA. 48,'1346) and bren-'
Previously relmrted lincedurts (loc. col.) changed V by '
zymIc tests. Exptl. details w4 to he reported later.
nivans of Ac,O anti AcOAg to lq%o Inactive Ct&I1#,QOCH-
' 171. S. Frfach
(COXONHAc, m. 71-3
(2,44mitropheny1hydrazofe, in.
'
105-7*), and thence by intans oCU13% (Kolloultschi et al.,-
e
X
fo- and efyara-vzcernatm
CA, 49~ 22954) t
. %76 mixed
'
(if 1, in. 00--107*.
600d. by tiastlonal cr sta. of the tri-Ac
y
The inixed raccinates (1.815 t.2 1. 00 ml,
clerlvs, (VI).
dry C If.N and U mi., AcO lript,48 lirs. at 20 , evapd. in
ftCU-7 at 40% and the residue,taken up in ether yielJed 2.05
'g. (01%) crude V1, in. 5G-70'. rractional rectystu.-from
Petr. ether 1b. 25-40*) acpd. 2 ccnnpds.. m. 80-2* and 65-
'res
p -raceniate of 1. m. 07-8* anif W
lcf. for the Arm
8:
a by Grob, d al. (C-4. 46, Mai, and Carter,
u~d
:

v
M:1' tt.-wl
N',

l6agmatka c msmws to N-meno- asiJ M,V-di;
iubxtftuted famml=. G. Ftxkw (Uuiv. Strgcd):-
4
Ack CUlm. Acad. Sd. Molf. V.-T[7:K=Xiu Huglish).-
Ilydroge"ting 1.54 C.- N-cyaw-20-th-r-buoykv,
btumyawtrjWr4 In W ml. anhyd, ULM ont I C. of Pd-C
9% PdO. addhis 3 tul. 3AN IICI W mhyd. EtOll.
filtenus, And evapg. OM fittratt to df vnm in mcks pv 1
O.IM S. M40MIMMoytUamocalts'--lict (1), cvtmlc" newles,
m. -114* ((rum HtOH-Vdr. ether). SimiLdy "em pccpd,:,
NI-plawyl-N-mtthyllannainkline (H) pkmte, m. 1-0'. an-I
Pkaawlate, m. 198'. N-pt" Urmamwine Pkratt, u1.
191% N4)tftyWacm=ldl*e (Iff) pkvatc. m. 172% im-1
pkronolate, m. 2100, N*:dd4Dnjiyj)ninrphi)liae, tr.
-bL 1,,:n. t74', ftw~ph R.,P..ApdEm~hi

. ~ ~ -~ . I t7i ! Is ~ -, : -,- , ~'. I , - , - - . ~ ~ , ;4

POT)CR9 0.
Situation of organic chemiatry in Europe. P. 193. MAGII.R, KEKMSOK
LAPJA. (Magyar Kemikusok Egyesulete) Budapest. Vol. 10, No. 7j July 1955
SOURCE: East European Accessions List (EFAL) Library of Congress
Vol. 5, No. t, June 1956

FODOR G.0 TOTHO J.0 KOCZORj L., VIKCZSs Iren. Rtmgary
2..;:
Annual meting of the Chemical Socierty In the Germen, Dwacratic JWpublic from 19-22
October 1955.
"Synthese von 6-Tropen-3-01,, ein veradArtes gesminsames Zvischanprodukt seentlicber
Tropswallvaoide"
80a. Cbmisebe TscbnUo Feb 1956.9 Una' sified.

Cid,
lli:'k mtL-r i t--e 7 '-rjlSLM!Y 44LL-va Uc-.4vc-~s
i
r

x" cpt'~:Av -3 Iii i t1`4
'
~'l Will
wIltarul vd-uh k~43ftfilQl

III 'c'-ptically active "I'Levi'mus by lall' in
a
'
~
alillyd. MiON rattw tham "~y m.p.
d
Qtfo. and try~
:"kl
phnt-~;rraphy- I -HCI (41;5 mAvxc4 r0th 12'a rrL
-
, resOve
2a tu 5
ofl
in
t
a
91
i
m
i
X
r
n
, r
i
w
c
,
.
f g.
,
o cx
y
%ratted vArjl 200:ad. H20 and KA"Ot and cmd.,with Etto.
Uistn'. of the extrgave 49.1 g.

198' lIff ~3231'
g. ICILCIChEt
k fukt, f 12.Z and 3Z
hWed ja a sAled ta!~e- at 70' fer AR hrs,, tht prWact

d aud recrystIl. from E;011-
v~ed with CHC
18.9 #.- 95-iuetax
t to gm

A mispertsna of 9"'Rrm AP-f; Oc 1 l 3.4
ML H-0 w5a sh-,Uq willi sAR ITA 11141;
fillmd -v~i- WRA 4: tim-with I'M tal

filtritc:w
id i
C aud evaod: 1-~tmstu~ of the
2.32 j., Ya*~-ar!,d~dhy&
cAlOoidA M"m. 210'
kirlir with

ad from
'AgAO in H14 tmtloa'- evu
rn.

WA
C41fa- iii &Wed ~ifrapviisa -in J_ ir; 3 3~ 3
13rCN
w af, Z: t ctzl
i6 hm . mate:. M~4, to give a5.63 vz.,Miw c. y~: tly
VnAhing =d emtg. T:t~O is ~-r I'I y_-it;
faiV --2-A' (12,015), toattliq Y;i,L JS g, 111, Ti ~a, _N'
.~Wml, If ~(J f. I S
hm., MJ VW~ UCI L-1
00 V-Il. lin,~,
midve lq%-is txfd, with 8 puticlas ~4
tiie.
-,t~ tz- 64jmL
nf Na0l.1c. Pvapu_ cx*n, %vith 261-1 111!. ~Il~,,._
-f-, tii. m EtCH I. Ul I -
Vrl tal. zT-.L-yd. Hu!"! L t
cvap.~i. i~-T ra-uc imli; tak~:fk LIv ;i
Ernj~ ClIal. Tho.. WW1 litco, dIc 71 !tit ~qp
were exld. with CTICL ~_-l ili,,-
- ~ --ivfr 1~ 1 1 ,
wu- drici:l fgS!j4l m6mfificd W~Th dv-j Ai~. IR I wi,l
-warwi, civs(n. d the rr~~, .
~tl'Uc inini
oft; F"rep. Ii:
-L~Sk (C
nj. ((IC,~COi: :1
~l hr-.. i.4 S
_(2.z! r-I Iq 2V 1;4L Ij__' Z, min. wita 3.4 g, I
wqld, Ag-D. C and; C~eapu. im
0.0-12". V111 (2.7~33. g.o 4,;A .j III.
C. , I I
tLe b1d), k,pl
arld Clrlul, iu I
vllic

2

lit
'~.Co vtod-Lz-13 id. 'A' A in L
ccrttrifuged; at Wlco-frce pfit. rvws' 5'
with 5 Ent. plimit arid -I'lul. Met NrA gitri
ety6t. telidue wl~ W'=hed With ifetco and ff(IIJI

led;~k 1-wome (I)Q, i:z. 2W'
:
A mict.
III ~Uj utl. 50% tkq. UvOll and (133 g. AgO i!k 10 in!. TIzO
,
4
AL
was
dfareA e kis
With 20 nA. c6ml. I fcfT&:' 2 hes. f, f kc~-Iml -d wl i
C and evapd. i.-; mugo to gm Oa20 g. Ma-cafteryiFfe"hy!-
ceiri", ?X), lit,
-
' ~M
m!
j~
d
6
-
em
upiti). ja
~0-
).
(
"
-i7c, n red -ix'
Phife mother hqu6r fr~in LK g, -Amp wlik wazi
tit-ited With A9tQ (f-min 1.7 C. AgNa,) arA a) nil, fl.~O
and fiftertd. 'I'lic jrcsidu~ o6 twapr- rf tillmo wit,; rc-
fluxed - 3 ha. with-~omcd. 110 and tiapd, Cry4tu. il, tilt i
(esiilue from McOlf-8trO ykldnd O.-Mg, X. coti, vv rtc-d hy
'
sbaking with
Aa), woxking upond rocryAQ, !rvill
f
23
h
M
i
E
o
cc
jik-e (KA). In -
tt
e
Impii.)
W ~
to, t
O
f
), Thc~ 11il
Me
f
i
d
3
tp: t
t Wca s
w st-
jig
fornr~ i~t racatio-ttA QwLtanizatina ca I pmluccs
in rof-Airii whcrcas therevusu
1 rives cotoilds. i" w2WO" ihe oewinal lcvu rututl4j" is mdll~
tahiel, or iticrcmwd. It craidv4d t4at tb~~ 1--touc IX
ii (jerived From
III,: thylti-op"u-'iIIIII
'
,
th
d
i
Vit
1
r
i
V111
N
ft.,
~e 1~
ts
at
e
atom ou
uv
t
u~ sa
t
t
4,
VIUC, mul X. Me vpf'44ite configuratioa o~wmrig in thr
quatemwy s3tts IV and V~ Thius, tho JY-Mc ~x-,-(ws in I
=1111'sud the crutip in Ifit. fi~--o
b-vc rtLw