SCIENTIFIC ABSTRACT KUCHEROV, V. F. - KUCHEROV, V. F.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R000827110001-1
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: December 30, 2016
• Document Release Date: June 19, 2000
• Sequence Number: 1
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

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(U.SS.k.) 14. u7j_4i(lqj4)._ &I Islas, temp. with gave Is),, I a
Kiptis. with I am I" b. 11 .00
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0 oil Willy di'lls, 1.6 lit) low Is" ollbs. 04. 11,41. 1 ll~ I IA&d Prot ft. Soo
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go I- pect-orm"I with ;Vlr; AA)l( low ir,.l no I ftog;~Iwn- tww "Mil.l., I-C, I.I. %,I,;
004 Wo"Ill Inwhr., .61 0% slomr, is a pink still.f. whitch. AVr; m"ol's I j%.`41.,(,, 1 600
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rh IM101011ting, its, A1,41, brigmer. too. (A."VOIAW.:
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AULJI
isgut 1.3 a. KOlt IwAltsl -sto a Stram Itath Ex 2 6 W". K%vV brv. ofavt 11.3". Ill the .110 #Awv. It, 1.4; 1#', go,
law MIP P140, [I,. 1poil-r. av 1AZU1. I tm*tA with ILIC- O%: 1A.W. 41." (l.Wt2: WMItACIV. the (."~Sttgj rt&l~
so
ICI Awl he'll"I fm a 61.16tto With (41r.1 hlr$. ing orree pirml.; fj &VAlsor -( 1U. Is I.'A 1, 2 % Is 1: 1.450 IV. -C- 0
tv I Nt*f I.. %Ili with Foils. dt1.Fr1=.1s0`r("I1W 401AS111; IQ OAM "I VAW-r filowkwA444. 1, Ilia 41'. Qt.
Ol Ill.." to Itia", wlti.h **I sgslsl~l glib IAVC% '11, of MI"; Ay 0411-rr .4 0-.r.,Pr1
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"fort tfrost~t wilk,161filit. 7.11 %*.*W I 4.M5.W.*4IMItm1 I I.- Vt Ilut .4
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.64. el-11.
40 S..
too
u
0 0 0 1111 0 0 0 0 Ills 0 1111 1111 0 0 0 0
0 0 0 0 0 9 9 0 0 0 0 9 0 0 0 0
10 00 0 9 #10 0 9 0 11111 00 0 of 0 0 0 1 Is 11111 0 All-4111 0 0-0 41111 0 0 0 -ft 46 0- 00

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--waaassawo l1advadves of the Cholesterol Met of

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ill 16. 1137 -42, 1 %1,1111 in Ru-",,)
a
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m

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(from pylictine-P.11C.CO). C, M. K.-IJAI.Ill

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Cor. wateir. and Sim I hr.; (Lt ppi. WAS ~vd." ;m4;r"Ib
Antim degiveds," M the hoteretrydie
Arl -00
taim derivatives Sat N. P. Kerfiev"a 1"; IICI and 1110. purification of the rvmkiM
00 -Sti tit-A K. A. Kortsenhhow. J. Geo. C&tvC_ (11-349.) is, was mr-
I-.tit -3~). -Tbkxwm (12AWT1.4 mospended in 4() m. romr4jobed by Sale. of 23.4 1. in 27.4 g. 71%, Now. 1*0
11,0 wa,& trevittif am 0.5 hit. t 20 C. 2-hromomMlo- triestrornt with 0.3 If. c1sturmal &old 04 C. NaStSoCiS. tw- "so
mlw h-fimt to bolifing 2 lin. and thisinif 1.5 hn.. filiert", aml aMitylog with 13 te. NO
L - *00
47t I., hNII Z101 ~`c J, .4 a o I a o .4, S,*. r 4&*d A joAN &- twA So - s -n mM" : yk&l M%. gn. 200-711". Twk (is Jr.) An 43 g.
wltr at of " with IU`o IN Mit and 11-4 11. ~Srtivmted charrood mW 0.4 g. Not-
~IVIM fig()); Ite'st"I"
v! vo et at 30-40 ". fallavred bYA0. woss miltmed 0.3 ht., cooled. Mcmd. treated with
rt"Init. gave of the "04111
00 0 Itsm (1). in. 87-8* (from Mcc-cv"Sed. 1110.1ben
Of ho
Water the" It IJII.V 8.) was Irmicd with 0.4 C. the rmte
00 At Noon. heated "it 0-4
At-P in 11, 9 cc. A at We% allim"I in Stand overoldho; **A purifISA by mvin. in 31
see
00 diter Suitt". of 141 tv. I IS.- prmfwrt wall 11firml and mr. r%nrrmJ am! D 3 e. NS*%(% to kmAing 0.3 for .. Mirvoid,
If_
I ec.
1l: WASIMI With water, I to."j-104 3 a T-&*Nkydvokmol~ cooled and Irmed with 10 1. COMA. IICI sea a. Ittl to
00 0 Ikiesak, M. I *-I " I (0.M j.) in A cc. nmYJ Ulams reaction; y1seld, ".2%. Sm. U"* (d. see
L'_J. it dil.
Pilo waa added to Ls. chdfttmjd gUareformak (13) in Steam ISM Klookow. C.A. 1111. 214,11; 111mmoo wid DW
Sled
00 111 ce. rip And The 16121. WAS A for 2 hn. Oaptmi, C.A. A 7a*). U. N -00
tvit 41.5% ekokshp)f 4 Stamm" Of 11-1190-3,40M 1161" vidde- ISO
"'Mytidlim vita d
(I it merco)
111440. N. F. KINCISCIM. '. F. Korhovow am X. A.
940 WILD Kwhorshkov. Ilial. I-A~141 goo
treated with 6 ' 0 to J10(le-dil E,10 18 gtwW dim commiessists with 01001hoct), 11) to lom! crefic dir.
0 &At to, 542% CAMEZ,41 d 4 . v0
4A4mAt-rivs. (Chkitibabin, C.A. 19. W). to-a-awAr-o-
At. ex-E I 4-2-31allak pridim and i1ad to react 109
rvirl"No Xmin C411s). 411 r_
(3.3 0.1 111 X10 ce, ssco we% trivated H do
30 cc. RI and allowed to otaniti for 3 4atrz9b. tram with farnaliton of nomerlic to wj At.
06,kiter LbImro-3-arnAwSpytithne J Iii If.) aiki 3 C. 1 4 1 Lt.,
'214"10 (fmm CAN-M 1 (13 to
libU.) I hr. to 170'. with Slow thatu. of the Pmhmg 1-40H,
C4IIpN was tivatedl vrith 20.3 g. jl-AcNH
in 24 cc the hosting wall continued 0.6 hr. at Iva' Lmd the pr"vert,
'A'CI over I tw- at below 33", dtcf Will& the ledlt- Was errid. by coWing. rep"waiftl 24 M~X0
111,011-70' 4 bro., cooled to 40% tMied with 30 re, powdet. idirmitilleti an too
a..
0 IV sea 105TL-X-
0 0 0 0 0 0 0 0 SO 0 010 0 010 0 0 0
0 0 0 :10 0 * * 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1* 0 0 0 0 0 a 6 0

dmi& a UG-71 (item lvtolf-CAN): UK aftahel julum
Am A ula. stoll pvv a
Fjv
(S-
-
1.
A*4* (fram I*tf.
ether). skmasirly, 14 g. W-bro-'i-2-stainapyticilm mul
00 20 a. I give after 2.6 bft. at 193' 34 g.

00 m. 238-9* (hom I,yTkiiae.
cu
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1931 1.4 C.
at
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W$4WlO
wid
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l
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rq m .244-6
(from FIOJI-
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)
=
00 4.3 - 4ki N-15-wol-ppuf )MdJddftdk
.
117-196 6roma (W. h 4
4 146-11
1. b4ado-24muipawkilm wm heated to W-Mu*

0.6 br. tiverv woo obtammd 83.8% of tbo gvrnipamlims
diem". 1U IW malonasmag J;&Uwljr hewrl wlib a. 00

00
*0 bru=&4 ka rwhw pvt 92%, of the "b8litutca
z: r 00
00 awlamu
t (I
X-) amd OA.S. 6-bnwA*4 bfttg4 45 rain.
-ft'n"- 00
to 190-3m Jki-fid 76
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Q
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iff
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nter
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wodwt Is oksimed Abu by the latetaction of a-chlore-2. 00
*0 amminoprddim with the cam Br4absticuted
a
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h
00

0.
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t
r0
OYM,
)UNLID"Mate (4
I.) In 17 cc. c4d cowd. 110 td to mand 2 da

MW After d1b. with caW, NI. twumaind with 3T
N.611 v
2
7 s
s
d of

00
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on beatin

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o
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-
1710
f
S
Oll
00 rm
t
(
similarly thm wm prtW. % 3-
)
0 (If= X.
00 Off-melco) (70214 S-br~-do"Now ine M.
-
dc" mi Iwo
ttfom Mesco) (W.570). 5.w4(#.:.
0
"ddxidOYFMiw M. M-P (ham EIOH). G. M. K.
91

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WO/C9
=K 9T Vewmns OPTXOXEM Runpodu8=00 m jo
",SW=oj M aq tm vto"Tq%*z=Ktzo-a o4 ow
-a-7[tT*,xxniq*;,o-,tuoqoldvozom To uO'rp.VVTxo ;0 d~nv
4nvTVmzw4ttT, wU **To%vMo=sqfto-a *&19 Vl;*u
vfflr (wiU00) nOzvTqzc=w
a; ZOaS Xq =T
On Tnorv !PVTZO 9nanv Itzia
'P= wo, - ago
gQT02vmc"lk*zdvajqm ;0
4M
-=a xTaq~ oj;~
ftTZTPTXIO ;0 TMM TvAQ=9 eq,:~ oeqTzaaga
ij 019 To,& urra qmpqo miM,
dd
,-
VQK -TO UrM 'XdvxQT4G= 0 TV-.U=Tjodxg jo qwl :.d
'ATa UTM g&O-TgqDUX 'I 'A mcgOT-10S 0,102VTIDO%
-UQS QRI~ ;0 OOPTJIUS TwxQL9S ;0 =jtpVTxO cUm

C4
AMIM110 i1strivelivitis 44 Ill~ 1100110r)WIt lialitnt, III
of anunsithistole. V. F. k&Khrr0v.
11411-17, Clkni.)
if
C-3. 41, CAU., "I". 40,1U, A 15
to 5.8 MjN)" In tits
1:1v lirt) at IWIO 1-Iling %luld a ClOrat An, am,
4-I.Ailig.
ill .,tW if tholls 1110) ykhf,
she Ne Mq, In. 1:10 W irrudri, its, 144) 1* (flown (ill,
%1,0111. -tAti-iiiis --mmillit with AeM.AtIllf virlif"I thr
ox-doo fit. 4NN W IfIt"n **troll,. S11114
lilt 1!;%js1-A- nt NO 7WI114t,
. Ir N it,, ., , A.-I.
~,Vj 11 ,'"1. 111 ptljjpjr). littiling 1.35 it
ami Ch s. ;) -br,"ok-4 Atro u- 1 -1.3.4 -its rahyds0-
plietmililirclic On dry Ntroll 5 hirs. save 80.3r; 2-amso.
decomp. 3104'
ItIAO)*. tFMtnltHt With 21)'~ %*&Oil, drYinff
the ppid. re.,let fite bait it% N. strul allowing this to stanil
overnight ill AW-AtOll state the :-Ortaw4a eadk.
sit. iffour Ili]. NletCO). IV. Syndmisiss of alkyl
deriv;tivtso(J.hydrozypyTidazWo. Ibid. IW24(IMI).7
Atidn. it( 21.6 X. %emicarinsside-liCt LM 18.5 g. '%**OAc in
130 Inc. &I"i Meoll to 32 is. 4-kelm'.64x,w A,Sd in W Inc.
Scroll gave after N ht*. of fcwm letup. 1411!7~ of she
'd4diteme. On. 157 W (.1evOwns.o.; lit.mi, 1?1011); lilt$
Pyrnilysell at DO lk)* all,) Pit 11 1. with %fCVCO gave III-I.
(NIM)MIde. in. N!, It', still 71 1,; MA, J-hydrezy-6.1"171.
U.-NOWlerl'.j. Sm"U. 1:41 1114tim"t.11% 14
Of 11,0).' 7-1,10hyi w1m.1.1tv
I'll the SOOM1.416.41kMe. III. 141-J' (JIM-41111IS ; ft-,nt
11,11-1
'Alik-11 state
..,.I 'I". Ake 61; j 414"111 1,
Ott. Al V III-I HP. 1441wit W K
414101,14.641-11f 4141; ~', 4 it I'll % I I N 11, 41. 1i4 Pit " Will dif-I
nill .Its; 11W dic I,- o-d g." %J, rAwwj
. in. A 7' litt'"I H(PIP, Wltk)J 11C4114 bit w
g4sr 76-,
1., IW,'- 7, t't
SSV* the III, hi .1'"l1 save 71'.
14,4TVIF.W. 41' 1.. 1%1 4'
I.

Isomeric tranderinatlaii of cubiffide of the far" Notice
IV. SYS669116 of abohmis. Need supbalk-Wissafilic -P 00
idds. %', F, Kucbetov. Zkor. ObtAwk! Khiav. (I. (kn.
0
~Ihtm.) 20. cf. C.A. 40. 71FAI.--The syn-
IfiClit 41( 'WACIOMMS iS OtAined by an allylk reannirmcn,
nt 411YINWIFICAftAnOll. Prapirisesiddri.o(IMS-fuffuril
I. :1111i ml. E1,0 Its 1101gOr (fixim Mi g. Xfg and AN) x-
Ilultri with ctxgini (utility 10% bitifin 4 3 bro..
I
%ith im, treating t Is uq. tAycir with ISk AcOll. "Ash-
ifig the Conildneil Off'. IAY1`15 With 1110, KICO~. Arid KA-
11SO., Cive -N%
InAlrel 3 hr*. with 10 ml. SIOJI cmig. 2.8 S. dry JICJ gave
111.2 Jr. M.S%) Aj 44400~104k. h, 90 W. *~, IXYLS,
it." 11,9578. whirb boiled with JbIrOll-NO11 I hr. nr.1
iculifi.vil SA%-c the fire arid, in, 71) 1 ' if he
mil.twir, i~-IlullgFlr rAve 77% ij*6177-
MI 2% it%,' 1.41M, (III O.Will, lirbling .. r. , ~-, ."
IA% Es
WAyl-4-kete.4tonsiak, fit 91 2% x1j 1.4.111) W- OVS1111
Per '111d. in. fol 2' (II(An 1*11. ether).
gave &wtkjl-2-jstykwlnIW, his IM IW. ywNling
4 b# 166 8'. wV 1.4975,
W., IJ495. free acid$ tn. Tfs-g* (from petf. ether). Butyl-
11-fitrykAthinig (45.1, 2(111 ml. *tn. ViOll, miul 1.2 nil.
Uh-. [[Cf (u.29 g. IIA pir, .1.) dw 6 6ys at r(xim temp.
XiVV 90% FJ bWYl-:-1%tY44?b4J1y1 fib". Ill 4-9 M', EV
I.4r0f. it.* Wgrln, whichwith KUftO, in itif. %jr,CO its th~
Mid Kiv" 3111*0 116 CIPOM 0,1111. bift :Crj 4'. N, 12.5 7 *.
xj" 14W21 if"O"L X.Ave Fj
IVAN.W:4LfAdlifff~j riker (MV7.), Ift iS 7'. xjr 1.44#11.
if.. all-lizell to .12% hir-fix Clit OM ClJi,11. Lp
ib 4 ", 1, 41 it ', . JP 1. 4270. if,' I (11.9W. G. it. K,

KUCHIROV* V.7 '; VOLODWi;'Z4Y6 - -
lyo~'.
Amino derivatives of the heterocyclic series. V. Condensation products
of 5-halogeno-2-aminopyridines with acetoacetic enter. J. gen. Chas.
USSR, '50, 20, 1890-1897 (U.S. tranel., 1937-19641, (HLRA 3:9)
(BA - A II A 153:83)

V. F.
a
o.- a-ar-O-,,.o acid dorl~latlvon. 1. 'N, -belvolw,
ani --o lyr V. F. Kacherm-a-0 A. 1. 1-.,ancr;,. ( .
r 113 9
SO; JoUMal -SZf Gengral Cheru,-tr,-- (Zhurmal Obrlichel Khl,--Li) voiu:-4 21, ,*,o.

c bow
to
-,,, zI f
7-Z J6
14
1.
00
'Ilk
Nil= 1 a d~mlglli
.49
r.
rd
V.

c A
Synthow of iffrilmoves of .1 Own* adds. I %*.
potomytowleelf dodwouvol 0( L~ "d it IYONO %, #I
Kudmov *)*,I A, L Ivanov 1, Gem Cirm, VA N R. 11,
I
JL9 V4 M51)(Flial Sv CA 46. 1111414
1.61)(PIA Ilia MInts It. R

ct
Amino 4wiv"v*s of tb* bsWwydk G*dOC VI
Dertiatim *I 34mUl-pyridealatint. %. F. hwhertiv
I GCOf ('Alw C.S.S-R. 21, 121V-.A(1V31XPn&l. tfAftda-
fiem k. - -.Sm C. I - 46. 30 Wlj~ H. R.

,4 -
Myna-M -of * d4linsives of O.&MI" sows, 11, Nov
of ormhower of an"" do a saw$ MA& W.
_Mawd M. 1. thorAbovs. /has. MAcArl She.,
-al. w21.3, IfL-A ;n, (K"x Tra"tim); rf. lk-ggaeana NMI
16. '072; la"*disd sholt. -A-Alk0-2~Wl-
tit I'ttl"I Irmo .4 - I
ptculs with KI.; tow IMINIucl. with SIII y6rul 4"AfIts. of
I.-.4miwim-ids 11W f'stbreting jet*v al ev-
14W14t Wide WTfV 1-11`1411 C41114:~ta"1411Y Irma 10%, inuviet of
POIC"MCOU in alk. Doi" at d 3': UL-1106110'(1) 73 3%
W. 73 a' (from We. relief). UL-Owwost
IW71 (from CCI,ptu etberl: lit.-Arseriaw IM:
M W. ve.-OW&AW let (IV 1 .4 %, in, Ila ", (Irmo CCL. lertf.
etb,r; To 0
s, I in dry jtO was ipie"I al -a in if, ji,j g
totent PCII. &red Offer nsf%t itmvf 13 t"iss, at 01 Anti I hr 41
U" , fillerni. felect 4 VOM I to memo with #Alw of
Pelt. 'Etberr. yielling 101,70
der"wrip. IN) I , (linen NW, 1; (of 'unfliers In sit Ow far bralin
If $We" Ct), noo lownre a high-whi
pertf,
!%milady. It Y"ll JP. UP.. dw V
1, =k"11111311 I :*.,,Sn~
4130' 4heal p tr. 91 1 't , uh It
4,~'-Xs-os4kg to 4 If vvv KA
.. I % 3.110
dote". DL..%'.((wbolw J)pbell.
ylnku*w OW I" in dry EW at 0" pir:8;2 DF~N
tWaik. iwbbd by d . *jib
tartu etbw M u%v cow; redulifis in also I be. YM& J-
Oh"Inip W-6, (Ir-ree clich).
A44n. with ver4ing cfF 3.5 s V let all reel. Will wal. isith
__ - _r - Y
al all o4 1%1L-W4IdP#-WY
4 h6 h. 1""
tv"I M I'M, "a '11, werlolvirt
lideerserwo. in III W .41114,411 %Tfp
Ili A%, M. I., pl..*mko,jodansk. in,
jan,04 ~041
cil.-korie"WiOlF IV in. IM A
syleaseils so Owslirt-Y4.
amide, 13,
J&W~ 1491 4. F temim re the 404 lows 4-
via 4~.. WIAV IW
&,jh,d fee p.We 11 ell The "i" Anered that smism
ifubuilutM few -,ph if, few Y-rti~vn. -tit, fiber exat"IMM"
Tb,.. add". to .1-401 nnitt 44 tht ann"r i'l '" Woll at
at"It W rel Itw flAkfeevil by
thr 41116W 4AI~ "I tier
be, .1 o)*. Ortif nep #v.%l,n 'a toe...
ell, ,I th, fecowl. -Skw.
ht . view thr
Law I he in N4,011. fhrt, -11-441 I..Ijml I
w Nw virld. Skwb a Well*
tit
of 110 (3 3 It ) Need 21
X,* I hp Md, .%'I/, "Al cel be-
L
feel :pl v P. Ofi-lor.
e-Wn

hiA k kk4l k3% N-1:11.4101 slarforyllp low (Im"t-jolief-
isomeskmamfor). be 110', MV IAT12. d-,- 119"1
stmiltier'. Ow Xpr onshog of I tow
Iub-the lanalas ;i I carr 16; 2'rNs, "Ar of
mwimp)- jV-*weAy1imwd"w4k. dewmp. W-104% wbk-b
O-Aver 54% b. 1311, NJ?
1.40MI. d" 0 9M). "We 2-11% 4MI66 011 94V* 11110" OL,-,
awtowN. "y1enjortmenoW. tne I;Wl*. nil I.44,-A I--
11110174. whk-b on IwoArAll"I olvendi" . Tow I -
fw"8TI sm"Altod #-1 1 pso !A% 0-
he IM ', IUW-193tillOt "Jill 4111-
lArlY. is*-Ame4IIl j&tV Ofth line COr""PAStIlliff tlL4daI"lWV
W)%. t4 IRPI". NJ?
@0w$,
%V IMAM, dl- Millelf.
I'kClfvcj($Nl(t
IM%. Is. llkj~
OI.Wh, d", I fam: it4we emorodo Oukt, M%. be rA .01
mv IA A10 MI). lm W2 3*). lint) fsj~.P-
eavide, camallig. 112%. be c"g. tin cotAins.
.:7" C., M. KIWAAAPOR

Chemical Abst.
Vol. 48 No. 9
May 101 1954
Organic Chemistry
,im"ji-aL POITcyclict"'pounds retated ts duatLs
xi tereochemistry of cydk campos4ds. 1.
-IW!Lof hj%jWjyIth titracanic and moucauk uM
-CAUSJO~ Cis-trans Of I
I d
s"V'th.
11.11. Ad. if' %"
1-7(Enst. trauslatim). CA. Mw
XIL Condensation of vick vft vjhyt Roma
and the trunstomarion 1. N-wasuff V-d
I - Zaviv(toy. Ibid. --M C.A. 47, MW
H. L: H.

XX ~ ~'
cetylene derivatives. M.
c0 do related to ste2do. l4151=eSvIf2pOOIIycyc:jcI
cycl c ketones with a-me"wlcyclopenta WO TWE. 1.
N asAw". VI F- K12 L. 11 .. jackbOYL, Bun.,
A.d. M. U.S.S.R., I Ir".i. .5cs. 19U, 427-3,XEngl.:
tMns at . C. .47. &M&* CXXVII. Synthesis of -
:olycyCHC com do related to steroids. Is, Structure;
f roducts a Condonsad of 2-inathory-1.3-butadiens
Ann I d m#thyl mothacrylate.
1. N. v and [bid. 043-T.-Sce;
C.A. 47. 1051U. vclk
chemical Abate 2'. Action of primary auto c MWOO M 119M[noohlr
ridine on vWjl allyl ketones. 5 thells of aryl subalituted
Vol. 46 NO- 9 1 d6od-40-6 and
May 10p 1954 -pr!4 N-. IN-
rov t . n. and V. A. nirn Yka
See C.A. 41~-~- cjmm7yqv~-C m~nM'
Organio GhemieUT 24. TfandwasolIew of
done. [Mi. 933-7.--8ft C.A.-48, j3V4. 1

USSE/Cnemistry - Acetylene May/Jun 52
Derivatives
"Acetylene Derivatives. Report No 126.
Synthesis of Polycyclic Compounds Related
to Sterotda. XITV. Syntbesis of Tetracyclic
Ketones With a Yethylcyclopentane B-Ring,"
I. N. Nazarov, V. F. Eucherov., L. N.-Terekhr-va,
Inst of Org Chem, Acad Sci USSR
"Iz Ak Nauk, Otdel Xhim Nauk" No 3, pp 442-452
The followirg reactions were carried out in
the course of this investigation: Conden-
sation of 2-methoxy-1, 3-butadiene with 1,
3-dimethYl-41-cyclopentenone, hydrolysis of
~_(l) 211
5-metboxY-3, 8-dimthyl-A5-hydrindene-1-91;
condensation of 5-methoxY-3, 8-dinethyl-W-
hydrindene-l-one with acetylene;condenzation
of 1-vinYl-3,8-dimethYl-5-keto-Al_ hydrindene
with 1-mPthYl-Al-cyclopentenone, with 1-methyl-41-
cyclohexenone, and with benzoquinone; selective
hydrogenation of l-ethyl-3,8-dimetbyi-6-ketohy-
drindane-l-ol; dehydrogenation of 1-vinyl-3,8-
dimetbyl-6-ketohydrindane-l-ol; cordensation
of I-vinyl-3,5-dimethyl-6-keto-Al-hydrindene
with maleic anhydride; hydrogenation of 5-
met:aoxY-3,8-dim~~hyl-A5-hydrindene-l-one; ccnden-
sation of 5-methoxi-3,8-dimethyl-hydrindane-l-
one with acetylene; hydrogenation of 1-ethinyl-
3,0-dimethyl-5-mathoxy-hydrindane-l-ol;
(2) P-;),OT8
L
10
dehydrcgenation of I-vinyl-3,8-dimthyl-5-
metboxyhydrindan-2-1-ol; condensation of I-
vinYl-3,8-dimethyl-5-methoxy-ib~-hydrindene
with maleic acid-, condensation of 1-vinyl-3,
8-dimethyl-5-mettioxy-41-hydrindene with P-
benzoquinone; and with 1 1
-methyl-A -cyclohexa-
now.

ITO
i.~oitwuc tratmfornmt!ons of c1101 nju-pr the fvudt~ iiartiff1i Lit rcm)m irta,, ater A hii,,r ji;i~~ I
v Tromfewumtinns of dIcyclo OxNvy tiry1carfAiii-L V. P i It 1011, vil"Ll.: :. $:I ? 1
IM'It. 0 1, " t it~ e C, ,
71CrJ'C1J`.C14(:w~I, wlil h h,- iii,A~ir,,I !!It 10
I I I t"""h"Cht"OA, I OIL,* A*
i;;IW 0; (.f .!rv IICI inio Zit g. I :I ~i'- I t. A, 1): 1, i it 1, 1
t Vm
%,Mid tlovly 711 K. Et PYt(WkIIcJt1' OUd the by lictti 9 th. -M -7- `i~ 1" -.'
1 V'111 ("0 '.'1 hrire., ywl,liti~. aftrx trk~.ilr-iit hilti ppt., m. 114 -51 ws-t t,it mi+:1. 2.3
I~A,A, Y-,; di,.-vtf (1), tit recrysti frinn 11, i:,kv'2 if
1,4: 1 it. I %fif Mfill wil 11. J%,S.~age of (try i (C I into I '- 7,
T~C TrjXZ, nil-ITYrd -01f.wei by J, d(1)3 -At mum tmmT. ~,- 1
"T, :1 (1 Malf:11T I i;~ull . . .- ,
6t "'W J daj.,i, yiOdit,F (), 0 1 Ll 4-t I lir-
.5 g. 11, ni, WX-2'. which wgis decatittid fr in pptd. M.0, -od. tvit!
It CIO, I 'I Actlif I I ha 130- at 60'.00. I'll Into 11,C). ..III wj,thrd WEITI
In. 157 ~'); the 111011wr 114tsor Jog 9 X. ilrb, nV I.,AJW5,
X.,Iu c
-1,, Ai- !,: ow,~d 3.5 g. pr(Atict, tit. furthi-ti whi1n. o' vf thi, with CIO, In AwIr
ing .1 1(41
III, I Iwl allu, , thr to rr!i It fisr.. 1,mittro .17) :J.
i.kitt I. 'try 110 1 "liti. it to 19 t. If.
hr. an a .itcam bath aid ev:ipll- rif the vil-miti r.;,6c li~ 9.
DI, When ery IlC1 was pawd 3 min. Into 2151 C. I In
c(CS1111h MI. MCICO and the milt. Wds refluxed & It:$. them v i's
It-hied 92 1. 111 guld 13% (Cj1,AC11COC111CYsCLMI;
It 33-71 yield lot this 9,-m wu ch-mlim'd WI= I_rfA3
rdi; HCI 8 ha.; a Onall qiOld d T
1.1 sq. CICO with cot, 'I
vm also Obtahwd. K:wAappIT
till)

St*t%Kbcnd%try of fd.c compa=ds'.' Ut. cis- raa
ON-mar 1. N. NA~.v &"-I v A p V-.
Afad. Sri.
49. b321JO. L.

Cstf., "Wmvq~Al-.- 11t m- v4d
ind tttL' f-,Irs, -------- -- --
40
famoiddiml-A. if N,4tqrL-V ATA V. i~. Kwhtr" (IN. D.,
ff-
--CL-C- 15 C~ di-stit =t
With
--- -- -----
--h,
vv'- --g-. dz~
gz M - & A-
with
Lw IV tAiwti da I.M4,
ell it the kbsir~uo. m. R&A~ If rom vtir. ahtr
pre
rAtn. of th't viter WiLEt frovev Pd k (tie of
KOW riac tu fivr (11), (C-cm, di'
wivd~, tht =td. eocc the emcipGadial satif.
04milied (Us),&comp. 2M-20 , sho obtiicwd by txydro,-
ge"onn of th~ urmad. acid,OVC4 Pd. R* luxing ?.& I - It
with 9-1 mt. AtCl 2 lim %ase 4A g. 11 cpkWpidi. m. IS&-O'
(cf. AWcr mout lkh%maclwr, CA. 44, wbkh by-,fro-
ON-45104 ~rtrratt~dintot thf Qwd(d.-,wi4 with AC! A*
-Abr.Ne. tho. wEdOomt. abs-

1" tit WA rZ, t/
McGH gKv- Z-kl-. 11 tileoij-He elkil, St. M WIA il hrir0-
4-pw, aik- - -t-4-
G.WAM m
32, --l" b-ilril .5 R!3KI I trwo
sad R~jlf x-Ifuslat.. id C. C45.Al -
12k. Efs(f-oku.
%W1, on bTdTQr-,~m0= P'0'4 tke MU. ;Aej;~C, Pa.
idmtkpj ww kwo xvtt4 OPEOL-aes (d C2
-r.WT ' '-' T,.t..t ; -:i.--
Vh"ct VIA Nkv~k 21, 4M6).
with CU'll. Cave tfe iri-
13 1. ".. !1miltily was rA,
(W). IN
%'S 1.44DO~ vkkt Mw (otw a" hT&OKration of
tht wirAtd. nUr am Pd. Re0=1ne : III wkk 7.5 g.
XrA tM 180 MI. UtOH lfk bM PV4t &S ~.Y-u dttr CYSPSI.
,,, nA. ifc2tint i
And"ificaaw. ivemoortypycM.Al
anhydrkk 2 bre. at W gAve 90 cif4wxv" at.
hmat" 4 (dkr*,cd t I
n asob"t esta (2 C.),
kt dry CjfI~ trrated with 2 tW. (C00)& S kri. at irme
temp. cave 119, C. H mopo4ff ukr Mhwide, ba IM-2.5.,
"I 1.4rio (hy"Yw wkk 10% PIAKUI im 10 W~A. PIT
t9); tnatutm k tha told w" MMG k StA VA-tt t1
p"f-Mf. frw wsowA4ik. to =41 (frew dit. M eW 1,

simitu'l', U4 mcaAfe "ter gmrr cmvcs;7arAj-jt asw-
41,~? ckLw~&. 4: t14 !-t. ', nV L4750. #xA t1tv qtc%u-kfr
awaft"ids. M. H64-5'. To I g. c*4U totma-V*
.L-Arr izL CKf WaA wwd I rid. (cM14 &*d tk, Slim kqi I
cruiedfatk-culd wkb
iPMI*. yielding abrmt 76%.
44iwim
ltwkm4f, am, 132-4~- simaw(y was cbuda:(l 11Z
tb,
t
he torres;Awrl f-iexj(ksiA. tn. I I Time-
'mczt at Cil-RIL 1%:oaO4 c esur witit (COCI), tmvlr tk cog- -
Uwufo. dt hquid. wfL;c!L rdImA--I 6
wt
Ith 5% NsOU-ovi, cii-na, m. 191-2"; tb~t titer
Cab 113-14', OS 1.4740, hat the ptoc-'
br iv=eimtkv. " an Lydrolrli~ it-
Trv_-tmeuto(tbqdigtdchlmIdc:
'With IMI't aia~;ufy rare thr tuxi-anifide- Ift: nkr ird
[Six-phearUzaw- Stalikuty r4-m "aw-jcr sizer pvc the
iftteT 410,~ 0.1ch to 61-11; d1ift. of
R
'thtchl"Oride, bf 11, -W, n't' 14A04. pvt at piqAuct wbkh
pt~ a mixt cd z!-c trsxi-432~Le
a lit *Ad it. -ilc
lit

I\' U C- 14 L- V, 1-.
NAZAROY. 1.N.; XUCHMV, Y.F.
Synthesis of polycyclic compounds related to steroids. Report no.22:
Research in the field of stereochemistry of polycyclic compounds.
Part 2: Samiesters of cis- and trans-l-mothyloyclohexane- (andj~l -
cyclohexans)-1,2-dioarboxylic acids and their conversions. Izv.AN
SSSR. Otd.khim.nauk no.1:63-79 Ja-Ir 154. (XLRA 7:4)
1. Institut organichaskoy khimii Akademii nauk BSSR. (Isters)

US,5R/Chemistry - Cyclic compounda
Card 1/2 Pub. 40 - 11/27
Authors I Nazaroy,, L N.; Kuoherara V, F.; and Andreyr,, V. H.
Title I The stereochomistry of cyalin coVounds. Part 4. Condensation of
1-vinyl- I -oyclohaxene with citraconic anhydride
Periodical i Isys AN SSM. Otdo khin, nauk 1; 73-M, Jan-Fab 1955
Abstract I A study of the diene condensatLan of 1-yinyl- -cyclohuqno with
citraconic anhydrW showed that the condensation products are normal
ortho- and meta-adducts. The products obtained through saponification
of cis-anl-qdrides are listed'* Unsaturated de-anhydrides and their
cl"cids were observed.to bydrogenate easily over Pt-catalyste into
Institution s Acad. of Sc.p USSR, The R. D. Zelinskiy Inst. of Org. Chem*
Submitted t April 6$ 1954

4AWd 2/2 Pub. 40 - U/27
AN DAUk 1 7a48 Jan-reb 19 5 5
lbstract t homologous saturated compounds which is zonnected with the screening
effect of the cis-substitutes an the-double-bond.-The-reaUte-obtainod-
#a lbad, -
MOT-611 --referend" i- -8 USM gulf 3 USA (1948-1953).

USSR/ chemistry Cyclic compounds
C^rd 1/2 Pub. 40 - 12/27
luthore I V*
No Andr*Mf
Title The stereochemistry of cyclic compounds. Part 5e Condensation of I-Tivyl-
I -oyclohuene with dizathyl aster of mesaconic acid
Periodical t I%v. AN 55M. Otd. Wm. nauk lp 89-97o Jan-Fab 1955
Abstract The characteristics of three isomeric trans-methyl - 4-octalinAj2-
dicarboxylic acids obtained from the condensation of 1-vinyl- 14_j~clohsx-
ene'with dimethyl ester of meBaconic acid, are described. It was establish-
ed that the trans-acids have an ortho-structure and are distinguished from
each other only by the orientation of the hydrogen atom.
Institution : Acad. of Sc.p USSR# The N. D. Zelinakly Inat. of Org. Chem.
Submitted 3 April 6. 1954

.69FAWWWREMN IF
Card 212 Pub. 40 - 12-27
Periodical 1xv. AN 33SH, Otd. khta. nauk 1p 89-97j, Jan-Feb 1955
Abetract I Hydrogemtloa of the trans-wid and its anhydride witi PtO rearlts In
the formation of Individual compounds the properties of which are
listed. Five referencest 4 USA and 1 USSR (1943-1955).

USSR/ Chemistry - Biochemistry
Card 1/1 Pub. 40 - 13/26
Authors INazarovp 1. N.; Kucherov,, V. F.1 and Andreyevp V. H.
Title I The stareacherAstry of cyclic compounds. Part 6. Lactonization of cis-and
trans- A4-octalin-11,2-dicarboVlio acids
,Pariodical I Izv. AN-SSSR. Otd. khim. nauk 2, 289 - 297, Mar-Apr 1955
Abstract vInvestigations were conducted to determine the laotonization of cis-methyl-
A4-oatalin-1,2-dicarbox7lic acid and to obtain data regexding the atructure,
of the cis-lac'%*Io acids which are formed during the lattenization process.
It was found that of &U the epimeric trans-acids only a certain group of
trans-acide is capable of lactonization. Trans-acids of eber groups haviing
double bonds botween the cycles are not lactonicable. Exparimental facts
regarding steric hindrances observed during the lactonization are explained.
Seven referencest 2 USSRO 1 Germ=# 1 Swiss, 2 USA and 1 French (1932-1955).
Institution t Acad. of So., USSR, The N. D. Zelinskiy Inst. of Organ. Chem.
Submitted t April 6, 1954

C)
V) V.
USW Ghemistry General chamiatry
Card - 1/1 Pub, 40 - 14/26-
Authors INazarov, I. N. , and Nuoherov, V, F.
Title IThe stereochemistry of cyclic cempounds. Part 7. Geometrical isomerism of
4,methylayclchexana-1;2-dicarbox.vllc acid
Periodical IIzv. AN SSSR. Otd. khim. nauk 2, 298 - 307, Mar-Apr 1955
Pbstract IThe stereochemistry of tri-subatituted cyclohexans derivatives - 4-metbyl-
cyclohe-lane-1,2-dicarboxylio acid - was investigated for the purpoej of
establishing the absolute geomtrical configuration of these cyclic compourdr.
The derivation of all four theoretically possible isomers of 4-methylhexa-
1-ydrophthalic acid through hydrogenation of cis- and trans-4-methyl-4-1, -cyclo.
he,-,One-li2-dicarbo.-4lic acid and its anhydrides is discussed. The effect
of heating and isomorizIng redia on the mutual storacnerical convereinne of
the four isomers ic wirained. Ten references: 2 USS'.R) 6 U."-'A" 1 Scandi-
navian and 1 Gorman (1929-1954).
Institution Aaad,-of Sc.9 The N. D. Zelinalziy Inst. of OrErn. Chem.
Submitted i April 6, 1c,,54

IVI%
ILUROF.I.N.; JrUCMOF,T.F.; VJUTOFA,G.P.
Research in the field of the steroochealstry of cyclic coupounds
Report no.B. Condensation of cIs-l-vInyl-6.9-4Umetbyl-&& -
-eyolohexanol with citracouic anhydride. IzvAI SSSR, Otd.khIm
nauk noJi487-5nO W-Je '55. (KM 8:9)
1. InstItut orgimichaskoy Wait im. N.D.Zellaskogo Akadsmii
nank SSSR.
(Cycloboxanal) (CitraccrAc anhydride)

U&CR/Chemistry - Organic chemistry
Card 1/1 Pub, 22 - 26/53
Authors! I "%zarov, I. N.9 Acad.; Kucherov, V. F.; and Andreyev, V. M.
WORM PREWWWWWW" i-
Title The stereochemistry of diene condensation of l-vinyl- A cyclohexene with
nh-rdr1:ds---a-hd-_1 *----
MIC-AW-1
acid
Periodical, i Dok.
tal SSW 102/4j, ~_751-7% Jun- 1,, 1933
Abetract I Interesting experiments. 1 data are presented regarding the diene condensa-
tion Of I-vinyl-A 1-cycloherxene wi *th valuic anhydride. It was foutid that
the condensation-is followed by the formtion of two possible steric iso-
mare the conversion of which makes it possible to obtain all four possible
geometrical isom4r's of --- A4-octalin-1.2-dicarboxylic acid.-.A study of the-
herma",nveruion"f-t-hoo"cl-da--showed-t,hat-t,ho-is=or-with-"ti-eit~
ra 8--is-the 'a iost stable and easily fomin ome
tion g Is ric -acid- -Eleven
11937 - - __ - )___
referenceet 6 USAs 1 German and 4 USSR 1955
Institution Acad. of Sc., USMO The N. D. Zelinakiy Inst. of Org. Chem.
Submitted March 29, 1955

t'4"64ittric Isomers of dec&hTdtW&9b4 -rMr-d(car
di-Iferster,a
liquid),
Wil ift acid and their ftaxisfarma,
'. L-- Thist.xtis peculiar to the Imari-dernhydronapht"k-nt COO.
V. P . I'Mr, 0v and V. hf. Amireev Qi. I
%
!;T U
S
S
R
b1 Makta 1
cd figuration at the I itfOR carbons.
76 "
-dro "
230'
l
t
dride cf the d
c
n
k

ke .
.
.
.
.,
Y
d. Nau S- - - - Of. 195F. 52: precteing al
c
, i
.
o
care a ncw a g
i 5
jr-
.
dru'r, in. 60% which probably has ti~.e cii-cwi-fill conficurs-
tr.-Condensatio (;f I'vinylcyckhexerle with m4leic ticin; its the cvrresrx-,nding
1
d
C
AnhydrMe rLnve 2 1 iniers 0 in. M4
, Which with
HO,, gave
i-Afe titer. liquid, Thean.
Clirboxylic anhy1ridti (1), m. 54" and a liquid, which hydtci-
zl
rts
to the &C4WfQ a6dS
M
dt
l
d
d h
d -hydritic with MrOll Cave the e%,j::701c (:!~r "ith 64-anti4is
ct)(16
"T
93"
tit"I "tttifird
t 2
tNi
f
i
hi
h
.
o
e
an
p..
genatt
,
,
y
y
1
112', all(] sn. 153% tvhk-h ate the cis-iyr-cis and trant-anti.
. -ca
a
a
ant
tu.
x)
c
4
, w
with &W)Na gave thcfree azid, tn. 26,3', ivliilr convratioual
cii &-ructure-.%. Stollo-He etUrs of I were subjected to isom- hatiexic of chain knzth at the 1-carty,)xyj ray,: -,he c(%rlt.
trization by, heating "Ith MCONa. Thus the xylt-cif spindilig d~ij-' in,

i=cr gave Jyn-cit ester esterified at the 2-carboxyl, while IAV, which echydroen-lifed '111,1 icc;al'~'%
L . Ylat""I if) I-
impt.-dric3tion of tho syn-cis df-He ester with KOH Kave Mec~llj. ls(nneritatinn G1 the (noru-Mr. t-,ttr (in. 91')
-wainly the sylt-cis mono-Aie ester estcrified at I-Cartwxyl; with MtONU ri:tve th! ptcvk."%ly &-skril-ij cis-witi-t-.atio
the former tster, in. 139% the Litter. tn. 120'. flyategZaa- dic:i-Ay.)xylk Acid, fra. 2103'. If)-drol),ii "t tile di-XIe ester
tion Xzve the ifewhydra analdes, in. jkt*, and 1'21% resp.
ON'
d the s
t
i
M
ter (
i
h M with I mote KOH give flit "wco-Ke. ell, P at the lc-Lrtxijyl
*
.
'
n
d i
i
d ti
i
9W
a
t
(
ze
.
snautt
a
t
ta.
a
e
Trratment wit
yielding
144'~
76")
di-Aft
ter
m
d
h
d xe
lar
er
c'
110
1e m
in.
) ail
's
wl. M. i
.
s p
Ile (twiliet, 60infrifM With MCON13, jpvc the knowu
t '18'
s
c6d
i
di
4
hi
t
ti
I
i
.
ri
es
.
e, m,
,
;
bmy,k acid, in. 218 (an
y
1
I
I
i
ith
M
d s-
ys-srams
1C
c
car
o
[
le
le
somer
-
. w
c
t1'
-'tat
t
i
h ClI
St
t
N
i
i
)

sorner
somet
ze
e ester
w
, Tile other tnono-
0
McONa and hydrolysted gave
jAakae-1,:-dkarbox 184 acid in 203' (4jtAjdride, w. 1381; .
rra
c
nt w
s
t-ditl
mono-
"
e es
et Cave M
c
o
j
Itaxi di-He titer, as. W. Artidt-Eistert tn&hod foe chain
itirs-rase gave, from this mono-ester. J-cv~rjv.v
.di-Ma ester, M. 4V). SQ;irly were treated the mono.
o
ffi-
e
ciff (
li
id (
Th
t
i acid, M. log'. which dehy,hogtoatel
2 M
d
l
d
t
b
C
ap
e
s
m
r
on,
iffurat
qu
esterls of wdi-tis cou an
dcrxr
Atc
to
t
iv. Thus of 8 W--,zh~ j%o-
xy
w
Cis) with Meolf gave the fto"o-Art ester, m. 137* (citterified
d trersof dec:ihydri~naphrh~ene-1,2-dicuboxylic acid, 6 were
'
to the traxi-
mainly at 2-positicts), which hytImCautte isolated and ldtntificd; 4 are of the ci
s " L-1 ari 2 of trans
(wid w4ra-Ma wit$. I'lure (A the Cis (sotners lie3ted to 2W* ue nearly
ester, tn. 95 , isonatrized with Aft.1DINa to the trans-asfti- quarstitAtivOy coarerted In I hr. to scries; tl:e

2
fro as itomer o( the frlie 1~; ~di-.Ve ester, in. 55%
~ ird'u-391i acid )iclds acid (as anhylittile).
-Me ester froull the
ly;1
amh~dride, M. 115, 1
. Y 'Mus the most stable is tile anti conaritaticm at c tcaus I
liquid anhydride I with I mole KOH Cave a asixo-Me timp, and 9 with cis Waricuration pf the lushydr;dc 6.,C (5 atomicl.
illiquid; t.y=ttockof this gave the corr"Pon4l tra
tlFxM`-
which failed to er-
dro stsda
e
h
th
d Th utikaawn 6omers cf the trwij seeks (feGxjy%-(raSz

d t
r
l
tl
th
b
)
e
lt
e
a
l,
y rans-syli-c
an
i
a
e spiweri
y ril
es Imita
le, (Cf.
G. M, K.

-7
F.- -

r7
nut
C'Iev, at,
A-
po -
-5--1 InI7-
1-4
104-
'Re, bit 9, T
ft " hr- ,!c 1;
Lttlt: f' 7;"-
off _0,44:
MW
al I; a, ME

~14 pl, r0l

TI-C I-thIT I J

:Ir

I! ;.M,
rrf-.

f4 fl 4 tq:.

Nnric: KUCHEROVp Viktor Fodorovich
DisnortfitJon: Research In the field of nterc-o-
chomistry of n1loyclic cnrboxylic
acida
Dogrec: Doc Chem Sci
Affilltition: Zn-ot indicateg
Defense Date, Plece: 29 mar 56, Council of Inst of Organic
Chomistry im,:)ni Zelinskiy, Acad Sci *
US IS R
Certification Date: 26 May 56
Sourco; BMIVO 4/57

~Si
give ter I!V RI.- yw,-r-wv
3L 710JI,
ME
-10 r. syn-61-7-kelolle Me e1
B wilb VW4, -;t th
117-~V t1rum Ut 0. ~ On "m-k jormc4 o--.hcaIL-9 Ilm
MC2 hall 1~9
laaime and ftomcr of U. ai.

/re
iy~--,*:
lhat C-TAY Lhe C10,11 :r.
m. 127-8~ th~ acio ,q), t-
Md esiff'. u2. 0-N
NIFJDII ga-t
71
aL
I vQPl. Of t'll
vp
tWn. pvc. ~-m aeidtfi=tian m,r
acha. M. lft,-tilical With
uld, m
Vn "In4ai -A-kU ("fit 4,tr,
:Tll"ZLI~g -th
Ilf 11-.-
I jAve
'add. 14entW with M Th-' lltvldl W~inf- d I~a Ilantl-mei,
rJono-Mee-Wheat-1411MUrly vrithAcOli IICI fav;! an un-
aystallimble cl-oomf. moduct; mIlmille 1 ~-2 "A,tcriml -ith
,A70 VC011 I.nd fl~f~!jying kave a Iovf yk~t 0!
11-frAdr-Ir tbt fiPlAnktis d;Wmxyj;: QcM
Ith Aeo-q-1fC1 (is abovC g2ve W.2Laly uIldlang"I
hi-in, 1-1 (Grim frgm
I

j~i~ X0 J-Ei. V, V.

41.

Q1

Rrl-up arl-I t hq-~ i,--" "."t i-m., I,-.- J :,i -

jxfAf flit-At vQM-W It- fqt!Pqw~m~fl tit d-u .1lew-

coil ~Jgum, tfo:l . An'! the of Ill-,
V4MITMIll. ~y T~- TITU-t XT~l F
rmcr Ia d 1. 1-.. 1 W
141%. W101 MrO.Nil-MoOli give
i!tvwuv, 211- I-vi In.-I'M
wifli A-z('l
O
N

1 rd2h fa v iylj /I 4re) (e,
m. n15-181. This v~jlb CjfjINI,F:%v* dt-NOe tAter
"f it ry-q. 'Irqlf~l' n- ~21
WIM zimun.
pzu I-
Tcf,
",ifiz lwv7hll.l .9
I Illb
-7-1011 f-11 tj-,l
EV, *A--V U!7 HhCr' T-zltiliCf,l
He 4 off '-N, , I
of tr;t

xy PI, ~f No t'~! -,r I.Al, 1:~i, A
FII Ja X tf- I 4L
C. _4 k a4 OAS
4

+0 MNT
c1; vrill,
uj
1;v

4L~
-ZIL

'r,~ ta

f 1
tuv&i ~U 3 1-1, Ki ""i T,11.YT I.,.
l` PPY '.V IZ
ILIllul
Q Inq P.1",
-ml ;k1 pp- 'I K(J. '""l1 rppl? ~!JEwKj JQ)rpu, .
w la
.11 (-) 'j
-
I- ti if ft i- ,
.~j p q~nj it ' (jw$W i w3 taw i
j

Mij Ax-rur.,j Y~)
J_m") anv4ezu aq.].

In"JI '2;~qp i1.."
HIly-
jj~ktl_l IA-14 ~1114 ;WI' '1111;101- IS':
4-ilm wl-L p, rt.~ i~ f';-, AAV:~ 6
m S 11.1"Wr .11U. V,_ pl- IL"t;j) v
dw ~j I!,pliq al
I -at U"ITI Wil T) '-ftlp"'t ;-11,
j I N. ~i ~ki i :b( I t~7 ti- -1 t",-) 'Jul
pfir
All p
j-z., -v PPI I ~T
l
_

IWO "pt, 1.~

drlI ml

t
t
, .1 ,,;, I I .
tlVi i~, :L,. , v . a -,j,
: - ~:, - ! 'j .
I - i :- . i- " ~ ..

IAZAROV, I.N.; KUCHEWT, Y.Y.; SAGA 1, G.M.
, `-i
Research in the stereoc hemiatry of cyclic compounds. Part 9. Condensation
of 1-vinyl-4a -cyclohexene with methyl acrylate. Izv.AN SSSR.Otd.khim.
nauk no.5:559-568 Mir 156. (MIRA 9:9)
1.1natitut organicheskoy khtmii Imeni N.D.Zolinakogo Akademli nauk SSER.
Orclohexezw) (Acrylic acid)

14AZAROV, I.H. -, KUCIIEROV, V.F.; ANDREW, V.H.
- W--
Research in the field of stereochanistry of cyclic compounds. Part 10
Steraschmmistry of the dieve condensation of 1-vin7l- &-cycishexene
with maleic anhydride. Izv.AN SSSR OtdAhim.itauk n9.6:715-722 Ja 156.
(MIaA gtg)
l.Inatitut organichasksy khimii imani. N.D.Zelinskogs AkRdenii xAuk SSM.
(Cyclehexane) (Waic ashydr!da) (Stereachanistry)

-HAZAROV I,N,-;-XU-HBROV,-T.F.;-ANDR9W, V.-N.
FQ
Ressarnh In the steriochowistry of cyclic compounds. Part 11.
Stersechouletry of A -ectalla-1,2-dicarboxylic acids. Izv.
AN SSSR Otd.khlm.nank no-71817-826 J1 156. %RA 9:10)
1.1natitut organicheakey khinii imeni N.D.ZellnskW AkAdauti
nauk SM.
(Acids, latty) (Stersochoulatry)

IIAZAROV, I.N.;KUGHEROV, V.Y.:ANDREYZV, V.M.
~-`- 1~ 717.-*710f.~-
Research in the stersochemistry of cyclic compounds. Part 13. Synthesis
and stereochemistry of isomeric dacalin-1.2-dicarbozylio aoidso Isy.
I AN SSSR. Otd.khim.nauk no*9:1091-1101 3 '56. (KLRk 9:11)
1. Institut orgunicheskoy khimii iment. N.D.Zelinskogo Akademii nauk
SSSR.
(Naphthalenedicarboxylio acid)

AS USSR
"Orientation sterique et structurale dans les condendationz dieniqws
de vinyleyelenes et stereochimie des produits de ces reactions," paper
submitted at 16th International Congress of Pure and Applied Chemistry, Paris,
18-24 JU1Y 1957

11 _--v- ~:
1 1- , I ~ : t
Si ~ If I I . ~ . , ~ .- - 11
I . - - , f e~ I
: ~ '10 , '' - & - , ~ " - 'o I
- -1-1. 1
-Ji,

~ - -L ~~

hie-
J.-M

62-1-13/23.
AUTHORS: Nazarov., L IT.; Kucherov, V- F.; Bukharov, V. 0.
TITIZ: Investigation into the Field of Stereochomistr7 of Cyclic Compounds.
Part 16. Stereocbemistry of Diene Condensation of Cyclopentadiene with
Citraconic Anhydride and Steric Conversions of Endo- and Exo-additives
(Issledovaniye v oblasti atereokhiwii tsiklicneskikh soyedinsniy,
Soobishtheniye 16, Stereokkdrdyapiyenovoy kondensatsii tsiklopqntadiyena
11 taitrakonovym angidridom i prostranstven" prevrashchaniya endo-
i ekzoadduktov)
PERIODICAL: Izvestiya Akademii Nauk SSSR, Otdeleniye Khimicheskikh Nauk, 1957.,
No. 1. pp. 91-99 (U,S,S,R.)
ABSTRACT% In order to study the stereochendstry of the diene synthesis, the
authors investigaged the condensation of cyclopentadiene with
citraconic anhydride ~Lt a temperature of 190 - 1950. It was fours
that the condensation goes in both possible steric directions and
leads to the formation of a mixture of stereoisomeric endo- and
exo-anhydridea,, from which a 30% yield of exo-acid was separated
arter saponifintion. It was alro ostablished that the.condensation
Csxd 1/3 at increased temperatures violates the principle of "accumLlation of
4
'7
I !,~ ~' / , /

62-3-4~3/23,
Investigation into the Field of Stereochemistry of Cyclic Compounds.
Part 16
Nonsaturizabilityll with the formation of an exo-additive. The
configuration of the stereoisomeric anhydrides Was confirmed by
studying the lactonization and mutual steric, conversions of the
homologous acids. Experimnts showed that the lartonization of the
endo-acid, regardless of the endo-position of both carboxyl groups,
follows only the -tertiary, carboxyl and that the gamma-lacto acid with
trans-orientation of the rethyl and carboxyl groups is more stable.
Saturated exo-cis-anhydride obtained through hydrogenation of another
exo-cis-anhydride (31) after saponification gives a saturated exo-cis-
acid which together with diazomethans, forms exo-cis-diester.
Card 2/3 There are 12 references, of which 2 are Slavic.

62-1-13/21
Investigation into the Field of Store ocho Irdatr-f of Cyclic Corpounds.
Part 16
A~SOCIATIOM Acadenq of Sciences of the USSR, Instibite of Organic Chemistry
imni. N. D. Zelinskiy
PRESENMD BY:
SUBIMM) i December 2,, 1955
AVAIIABLE: Libr&-y of CfV.6-"L4I,4
Card 3/3

' ''4
!%
yUGOSTAVIA/Orgmae chemistry. Synthetic Organic Chemistry.
Abe Jour: Ref Zhur-M-4ya) No 22., 73969-
Author I.N. Nazarovp V.P. Micherov, V.M. Andreyev., G-14.
Segall
Inst
Title Upon the Spatial Directivity of Diane condensations
and Stereochemistry of Cyclic Carboxylic Acids.
Orig Pub: Croat. cbem. actap 1957, 29s No 3-4, 369-392.
Abstract: Trans-1,2-dimethylbutadiene-l,,3 (I) was prepared
by the dehydration of methylethylvinylcarbinol at
300 to 310 5 o~oMgSOI, yield - 50 to 60ep, boil. p.
76.5 to T8Q,, n D - 1.4515. Boillng (4 hours) 51.5 g
of I vith 56 of mal in anhydride in CIH#reeul~led
in anhydride fin) ofecis-018-3p4-dImethyl-
cyclohexonedicarboxylic-1,2 acid (IV)p yield 56.5 g,
Card 1/14

YUGOSIAVIA/Organic Chemistry. Synthetic Organic Chemistry.
Abs Jour: Ref Zhur-Mmlya., No 22, 73969.
malt. p. - 67 to 680 (from ether - petroleum ether),
17.3 9 of IV, melt. p. 172 to 1730 (dissociates, from
water) was obtained from the mother liquor by saponi-
fication after separation (if III. The boll. p. of
dimethyl estel of IV (V) is 122 to 1230/5 mm, n~OD
- 1.4750p dt 0 a 1.0987. The thermal isomerization
of 111 (210 to 2150, 4 hours, NZ flow) in the pre-
sence of diethylaniline led to a mixture of substances,
boil. p. - 186 to 1WO/35 mms n"D - 1.4950, from
which cis-trans-3 4-dizetbyl-_/_Nf -cyclohexanedicar-
boxylic-1,2 acid NI) was separated after saponifica-
(from water);
tion, yield - 60%, melt. p. - 160 to 161 C
anhydride of vi (vii), melt. p. - 46 to 47 (from
petroleum other); dimstV1 eater of VI (V~I), boil.
P. 116 to 1176/5 mm, a, D - 1-4730P d 1.0921.
Card 2/ 14

YUGOSIAVIA/Orgenic Chemistry. Synthetic Organic Chemistry.
Abe Jour: Ref Zhur-Xhimiya, No 22o 73969.
2-monomethyl eater of IV (IX)o yield 3-1 g,, melt. p.
114 to 1150 (from etber + petroleum ether, 1 : 1)
end 2-monomethyl ester of VI (X), yield 1.05 9,
melt. P. 112 to 1130 (from 5*ual CHAOH) were pro-
duced by partial saponiftcation of 4.4 g of V and 1.9
g of VLT1 correspondingly with 1 mole KOH solution.
Trans-trans-3,4-dimetbyl- /\ 4* -cyclohexene-dicarboxy-
lic -1,2 acid (XI), yield 0.9 g, melt. p. 149 to 1500P
and Its trans-cle-icomer (XII)o yield 0.4 g, melt. p.
184 to 1850 (from water) were synthatized by the iso-
merization of 1.2 g of Ix and o.6 g of X correspond-
ingly by boiling with CHsONa and absolute CH30H and
following saponification. The Melti poin a of XI
and X11 anhydrides were 100 to 1010 from other
petroleum other) and 100 to 10V (from ligroin)
Card 3/14

YUGOSIAVI:A/Organic Chemistry. Synthetic Organic Chemistry. G
A~% Jour: Ref Zhur-Nhimlyap No 22, 73969.
correspondingly. Cie-cis-1.4-lacto-3,4-dimethy16
cyclobexanecarboxylic-2 &aid (XIII) was obtained by
beating 5 g of IV (i hour, 6og) in glacial CH~-COOH
saturated with B01 (gss)p yield 3.4 g, malt. p.
186 to 1870 (water), the melt. p. of the metbyl ester
thereof was 109 to 110 0 (from 70%-Ual CHSOH) - Under
these conditiobs, XII (0,9 S) undergoes a preliminary
cycle cdaversion producing trans-cls-1,4-lacto-3,4-di-
metbylcy*lohwuwe-carbcvwlic-2 a,aid (XIV) in the re-
oult of a following lactanization, yield 0.55 9,
melt - P. 154 to 155 0 (from x~-usl squsous acetone) -
Methyl eater of XIV, melt. p. 57 to 58 0 (from Petro-
leum ether + ether) produced XIII by isomerization
with CH 3Oft and follming saponification. Similarly,
Card 4/14

YUGMAVTA/Orpac Cbemistry. Synthetic Organic Chemistry. G
Abe Jour., Ref Zhur-Rblmiya, No 22, 73969.
2.5 g of VT an lactonized into a mixture., from
vhich 1#1 g of cle-trans-,2,4-lacto-3,4-ametbyi-
cyclohexanecutoxylic-1 abid (XV), melt. p. 199 to
201 (from 15%-Ual aquems acetone) was separated.
After the separation of XV) the mother liquor was
treated with CHIN4 and 0.75 g of aster, melting p.
63 to 650., vas,6btalnadj that eater, after saponi-
ficationj, produced cia-trans-1,4-lacto-3p4-dimetbyi-
cyclobwcanecarboxylic-2 acid, yield 0.6 gs melt. p.
161 to 169 0 (from vater). Under the same condi-
time, Xx (2.f g) produced only 0.7 g trans-3,4-
dimethyl- a -cyclohexenedicarbwylic-1,2 acid
of melt. p! 161 to 1621 (from vater). It we
established that the catalytic hydrojg=ation of
2-15 9 of IV on Pt in CH9H proceeds spati&Uv
Card 5A4
YUGOWAVIA/Orpnic Chwdstry# Synthetic Orgenic Chenistry.
Abe Jour: Ref Zhur-Edmiya., Ito 22, 73969-
selectively from the side opposite to CWH groups
wA led to cisacle-de-3 4-amethyloyclohmned1-
c&rbwq1ic-1f2 acid (XVI$, yield 2 g, mait, p. 187
to 1880 (dissociates, from 50%-U&1 acetme). 10
g of III vas, converted into 9.6 g of anhvde of
XVI (4VII)j boll. p. 145 to 146c /5 =1 n D . 1.4835,
d ~-Zv a 1.1435 In a similar vay (but in CkHl,).
Boiling of 5.9 g of XVII-in absolute CH30H led to
1-monoweth 4.25 relt - P -
,,yl ester of XVII yield
110 to in (from &)~~ CHSOH) L5 g of Vhich
yielded 1.2 g of trans-cle-cia-3,4-dimethylcyclo-
hexanedicarbMlic-1,2 acid (XV111t) melt, p. 183 to
184' (from vater) by Isobarization vith CRjONa and
foll.oving suponificationj w*7dride of XV111, melting
caxd 6/14

YuGoarAm/orsanic Chemistry. Synthetic Organic Chemistry.
Abe Jouri ser a=-Khimiya, No 22, 73969.
acid (XXXIV)p melt. p. 183" (frcm acetone) was
precipitated by the dissolution of 3-5 9 of XXXII
in a eous N&OH and VAlowIng acidification wl J2
HCI racid)j while 1.5 g of XXXIII produced ebloro-
bydrin under these conditiocaj eblorobydrin con-
verts at 1300 into 1.1 g of cis-ois-trane-cis-214-
la'ato-3,4-dimetbyl-5-chlor,o-,cyelohexwiadicarbMlic-
1-soldp melt. p. 173 to 174* (from.w%-ual acetone).
The corresponding 5-:keto acid (XXXV), yield 1.2 g-,
melt. p. 1139 to 3909 (from othylacetate) vas synthe-
tized by the oxidation of 2.8 g of M=V with CrO 7
in MWORI metbyl ester ot XXXV, melt. p. 92 to
936. The reduction of 2 g of WV according to
Klemommen prddueed a mixture, from which 0.25 g of
card 13/14
YUGOMAVTA/Orginic Chemistry. aynthatic Organic Chemistry.
Abe Jours Ref Mur-Xhimiyas No 22., 73969
cio-clo-trans-3#4-di=tbyl-cycloboxanedleaztoxylic
1j 2 acid, molt. p. IM to 1670 (from. 2V,*-u&1 sce-
yl enter (=rVI)P
tons) vas procipitatadj dimeth
boil. p. 119 to 120/6 m, n4 " D -a 1 -45W - XXXVI
produced MaI by Isomerization with CHJON& and fol-
lowing saponification. The oxidation of anhydride
of syn-cis- 6A -octalindicarboxylic-1,2 aced
.ICOOOR tn ClIC13 at 0' also
(12 g) with 9*ual CH
re ulted in a mixture of oxides, from which 6.6 Of
I -oadde, melt. p. 161 to 162 0 (from benzenell
and 3*7 6 of A, -odds, nelting p. 82 to 83 2 (from
other + benzene) were separated. A review of works
of Nataroff and coworkers concerning the study of
diene condensat~.on of vinylayclones published earlier
is presented.
caxdq 14/A

AZITHORSt Kucherov, V. F., Berazin, 1. V., Wazarov, 1. 17. 62-2-9128
TITLEt Investigations in the Field of tht 3tereochemistry of Cyclic
Compounds (Iosiedovaniyo v oblasti stereol-.himii tsiklicheskikh
aoyedineniy). Report 191 Infrared 3pectra of Cyclic Lactonos
(Soobahcheniyo 19. Infrakrasnvy,.- t;i)n1:try tsiklicheakikh
laktonov).
PERIODICAL: Izvootiya All SSSR Otdeler1yeKhimic~ieskikh ffauk, 1950, Nr 2,
pp. 106-191 (USSR).
ABSTRACTs As was already shown in a paper pt *7jllshed earlier the method
of infrared spectro8copy can oucc~.isfully be employed for
proving the struoture of lactone- For the purpose of the
systematic investiCation of the d(:)endence of the infraree-
spectra on the structure of diver:-i polycyclia lactone3 the
authors examined the spertra of tl;) carboxyl-frequencies. They
determined some structural reL:ulailties of the carboxyl-fre-
quencies of this typa of . On the basis of the ana-
lysis of the infrarod opectra of .~aatones-l and 2-methy1docal-
ine-1, 2-dicarboxylic acids their confiCuraticn was deternined
and from it the conclU3iC-3 Or, th, stereo-.hemistry of the diene
Card 1/2 condensation of l-viny!-2j-oyr1o1;-zane with citracoa anhydride

InvestiCationD in the Field of the of Cyclic 62-2-9126
Compounds.
were drawn.
There are 4 tableo and 10 refferences, 6 of which are Slavic.
ASSOCIATIONt State University imeai M.V. Lom6nos.7)v, Moscow (1:03kovskiy
&osudarstvennyy imeni Lomonosova) and
Institute for Oreanic Chtmistry AN USSR imeni N..D. Zelinskogo
(Institut orraniches'-uy khimP'. Imeni N.D. Zelinakogo Akadfjmii
naulk SSSR).
SUBMITTEDt September 7, 1956
AVAILABLE: Library of Congress
1. Stereoehemistry-Cycl-le compounde 26. Lactones-Structural
analysis 3. Cyclic compounds-Structural analysis
Card 2/2

F
A11THORS: Nazarov. I. F. 2 - 2 - 10,121,
;try of Cyc ir,
TITLE.- Inve3t-ationm i.,l tho F-l'uld oli
Compounds v OIA.a,J!. I,oiklich~~ ki4h
1P
a oy,-- d i n e n iy Ile,,. o 2 (j "1, 3,, G:cidi% licn
f ~xcnp-
by Peracetic Aot4 o
-2,3-Dicarboxylic Acld,,i and D(, iye
20. Stereokhirt 01. - alc%i ',jLjc,,o-. izzo~-, myth
1 4 - a nd om e t i 1 e r._~ - t o i! - 1 r) L: e'. ,l c:,, - Z 'L'.z a r'.-. o.~c %-.7h 13 1 o t i !.' kh
proi%vodnykh).
FERIODICALt I2,-reotiya Ali SJS.,q Otdeli-.~A3re .".i 195C , 71. 2,
pp. 1.92-199 (USOR).
ABSTRACT A3 was already slicivin r--~,a-tj-)rs of -;,~ zdllit :on
comi,ound of the dci;ble .--f 1.2,2)-
,~, 11 - ~ L - - 7 ',. 1~ ~~ ~ r, ., 1, t! -e al i z
-heptanp are --:y
e d f r om t h 0 5 i 13 f t 1 -., For tile
r "lip
it vimi of intemsl , t :~j , - - !" ,
n of tho Cho- o r,
Oxj.datio
-2, by
a-il. Espeoially i.,. t.,; e~ c ni, i--I r~t i c of the
Oxid-ition cyr-.Ie r--ati 1)e f i
,ard 1/3

Investit;actions in the Field of thQ 52-2-10/26
Co-,.,.I.ounds. Report 20t Th-?
by Peracetio Acid of lso,%,eric
-2,3-Dicarboxylic Acids anl Theil-
mac+,44 on-, of '-w--tor ~~o and Thereforr-- t1he
a73ove-,:ientioned LK7,IL LL I ii, of th~,
o X i d (I _q f o 1, 1.11* 17~ It wa.1
shown that tht! 07-idulic-n r~f --Ac-
acids (referen,:iej ar! ts of free -anda-
-car'-) oxyll.-Group S tla%-2-3 ;,,,LnL-- the formation
Of OXY-Pla~,to-acidA 5 nlid 9). Dy :.,ea:-.s ~,f layd:~o-
Eenation of the oxide.,; !'I %:-.i 20) u:lder pressure
the hydroxyc3tuzo ~-oi-r,~!!-, on4.~r.Z 22)
were prcduced with a hiL). 0-i o:~.l,!_~tic,n of thum by -.hrom-
iu--- anhydride the ccrrr-.,:. fcrm (references
23 and 24). By m~!an5 ~f C"her it
was pro-,ad that tho cxidattor. uf isc:112ric I.A.-cuLdomethyl-
ene -cyclchexana-l derivativ-
, 3
es t ' es pla:~e fr.~m to ox-:.-Jes with mr, exter-
nal po3ition of tti~, arc, !I referen~-es, I
of whirli i3 Slavic..
ASSOCIATIONt Institute for AN U~1'32
Card 2/3

Inveutif,ationB in the Field of t%e Stereoche:aistry of Cyclic 62-2-10128
Co,-.ipounds. Re~-,ort 201 The Stereocheniatry of the 9xidation
by Peracetic Acid of Isomeric 1,4-Endouethylone-&-Cyclohexone-
-2,3-Dicarboxylic Acids and Their Derivativan.
(In3titut ori;aniohezl-.o;r lchimii imani '.1.D. Zclina%ogo Akaderdi
nauk SSSR).
SUBIUTTEDt September 7, 1956
AVAILABLE-i Library of ConCress
1. Stersochamistry-Cyc3le compounds 2. Cye]Ac compounds-Structural
analysis
Card 3/3

62-58-3-12130
AUTHORSs Nazarovj I. N. , Kuc Bukharov, V. 6.

TITLEs Inveatigation in the Field of the Stereochemistry of Cyclic
Compounds (Issledovaniye v oblasti stereolchimii tziklicheski'J.
soyedineniy) Communicatiop 21. Oxides of the Isomeric 1,4- .
-Endometbylene-2-Methyl- A~-Cyclohexone-2t3-Dicarbox;~lic Acids
and Their Reactions (509bahcheni-e 21. Okisi izomern~rkh 1,4-
-endometilen-2-motil- A~~-tsil-lot;eksen-2,3-dikarbonovykh
kislot i ikh prevras~,Jheniya)

PERIODICALt Izvestiya Akademii Nauk SSSR,Otdelentm !Mimicheskikh flauk,
1956, fir 3, PP. 320 - 334 (USSR)

ABSTRACTs As it was ahown it, previous reports, the oxidation of the
isomeric dicarboxylic acids of the bicYc1o-(1t2,2)-heptane
series leads through peracida to relaxing oxidations and
to the oxo-configuration of the oxidation cycle. For the
purpose of a further investigation of the ntereochemistry
and the direction of the above-mentioned reactions the
authors investigated the conversions of the oxides in the
Card 1/2 example of the isomeric 10-endo-nethyleno-2-methyl _45-

62-58-3-12/30
Investigation in the Field of the itereochemistrj of Cyciic Compounds.,
Communication 21. Oxides of the Isomeric I 4-Endome thy lone- 2-Me thyl- zN:)_
-Cyclohexene-2,3-Dicarboxylic Acids and '10heir Reaction3
-dicarboxylic acids jind their derivatives. It was shorn
that in the oxidation of the endo.anhydride by acetic pe!.,--
acid in chloroform only an exo-oxide can be obtained with
good yields. The authors proved the structure of the iso-
meric oxy-^(-lactic acids. They further showed that the
inner-molecular lactonization over the oxide ring mainly
takes place over the tertiary carboxyl-Group. There are
5 references, 3 of which are Soviet.
ASSOC TA TION iInstitut organicheskoy khimii im. 11. D. Zelinakogo Akademii
nauk SSSR
(Institute for Organic Chemistry imeni N. D. Zelinskiy)
AS USSR)
SUBMITTEDt September 7, 1956
Card 2/2

AUTHORS: Kuch,;irov, V. F., Segall, G. M., 62-58-3-22/30
_9_az_a_r0_v, ' r-_797'
TITLE: The Stereochemistry of the Oxidation of the A 4_ 44-
Octaline-Carboxylic Acids (Stereokhimiya okinleniya
oktalinkarbonovykh kislot)
PERIODICAL: Izvestiya Akademii Nauk SSSR Otdoleniye Khimicheskikh
Nauk, 1950, Nr 3. PP. 367-36; (usn)
ABSTRACT: It was of interest to the authors to investigate the
stereochemiatry of thu oxidation of the above mentioned
(and of similar) acids by means of acetic acid and osmium
anhydride. The investigations carried out showed that
sin- ELnd anti-I& 1-octaline-i-earboxylic acids produce
individual a-oxides with good yields in the oxidation with
peracetic acid. Their configurations coriaspond to the
disposition of the oxycycle which is opposite to that of
carboxylic acid groups. Such a configuration of the a-oxides
was proved by a number of stereospecific reactions. They
made at the same time possible the 3ynthesis of stereo-
Card 1/2 isomeric 4-ketodekaline-carboxylic acids. See formulae 1-13.

The Stereochemistry of the Oxidation Pf the 4 4_ 62-58-3-22130
Octaline-Carboxylic Acids
Different from this the oxidation of the sin-cis-6 4_
octaline-1,2-dicarboxyli^ acid takes place in both
possible stereo directions with simultaneous formition
of isomeric a- and P-oxides (see formulae 14-18, 19-25
and 26-30).
There are 5 references, 4 of which are Slavic-
A3SUCIATION: Institut or,-anichoskoy khimii im. N. D. Zelinskogo
Akademii nauk SSSR (Institute for Oreanic Chemistry imeni
11. D. Zelinsk iy I AS USSR)
SUBMITTED: October 16, 1957
Card 2/2

AUTHORS: Shidlovskaya, A. N., Syrkin, Ya. K., Correaponflng 20-118-5-33/59
Member of the AS USSR, Nazarov, I. N., Member of
the AS USSR, (Deccased),_~!~ ~herov~_V. F.
TITLE: Dipole Moments of Ethers of the Isomeric Cyclohexane-1,2-Di-
carboxylio Acids (Dipollnyye momenty efirov izomernykh
taiklogeksan-1,2-dikarbonovykh kislot)
PERIODICAL: Doklady Akademii Nauk SSSR, 1958, Vol- 118, Nr 5, PP- 967-969
(U5.9R)
ABSTRACT: Usually it in proceeded from the fact that the fauteuil-like
configuration with a maximum number of equatorial subetituants
is the most stable. This assumption was chiefly confirmed by
the investigation of different cyclic compounds which have
methyl and hydroxyl groups as substituents. In this context
the investigation of such compounds is interesting which
have more strongly polar substituents (references 1,2). In
the series of the 1,2-substituted cyclohexanes 3 isomers are
possible: a cis-isomer with an equatorial-axial position of
the substituents (a - a), or a trans-isomer in a diequatorial
Card 1/4 form (all - 9) or in a diaxial form (a - a). Dipole moments of

Dipole Moments of Ethers of the Isomeric Cyclohexane-1,2-Di- 2)-118-5!-33159
carboxylic Acids
lo substances, derivatee of cyclohexane and cyclohexene, were
measUred. The tables 1 and 2 show: structural formulae,
temperature constants, complexe poarizations P,,, electronic
polarizations PE,, orientation polarizations POr , and dipole
moments. The comparison of the latter of the isomers of the
cyclohexane and cyclohexene derivates showed that the double
linkage causes only slight changes of the moment for the cis-
-form an well as for the trana-form. The dipole momenta cf
the isomers of the monomethylether of the cyclohexane-1,2-
-dicabonic acid are 'decreased as compared to dimethylether.
Parhape this can be explained by the formation of an intra-
molecular hydrogen linkage between the oxygen of the carbony'.
group and the hydrogen of the O-H group. It is interestinr
to compare the dipole moments of the isomers of the methyl-
ethers of the cyclohexanedicarbonic acid with those of the
ethers of unsaturated dicarbonic acids (for example the di-
ethyl other of maleio and fumaric acid). The difference in
the radicals of the ether group is said to have no noticeable
influence on the value of the moments. As is ahown in
Card 2/4 publications (reference 3) the dipole moment of the other of

Dipole Moments of Ethers of the Isomeric Cyclohexane-1,2-Di- 20-118-5-33159
carboxylic Acids
maloic acid is greater than of that of fumaric acid. This Is
moreover confirmed by the cis-configuration of the compound
number 3 (table 1). Table 2 shows moments of molecules which
differ from those treated above by having an additional
methyl group at C . As could be expected for the isomers 1
and 2 equal valuei of the moments were obtained, as the
moment of the CH3-group in equal to that of the C-H group.
The isomers 3 and 4 have somewhat greater moments. Isomer 4
is also the most stable. All other isomers are finally truns-
formed into isomer 4. Contradictory to the formula (references
4-6) the authors maintain that for substituents of the type
of ethers of the cyclohexane-1,2-dicarbonic acids whica con-
tain irregular groups the moment of the diaxial isomer (a-a)
may not be set equal to zero. In order to determine the con-
figuration of the Isomers of the dimethylethers of cyclo-
hexane-1,2-diccrbonic acid the dipole moments were computed
by aesiming a free rotation of the COOCH groups taking into
consideration their direction as irregular group1s in relation
to the cycloh,,xane nucleus. The moment of the isomer a-a was
Card 3/4 determined an 2,3o D. The experi2ental value of the moment

Dipole Moments of Ethers of the Isomeric Cyclohexane-1,2-Di- ZC~-118-5-33/59
carboxylic Acids
of the cis-isomer lies between the computed values 2,51 -
- 2,30 D. The experimental moment of the trans-isomer (-2y14)
does not correspond to the computed value of the moment of
the isomer &-d" if a free rotation is assumed. There are 2
tables and 9 references, 2 of which are Soviet,
ASSOCIATION: Mookovskiy inatitut tonkoy khimicheakoy tekhnologii i=.
M. V. Lomonosova (Moscow Institute for Refined Chemical
Technology imeni M. V. Lomonosov)
SUBMITTED: October 1, 1957
Card 4/4

J)'"HOh J: --ov, 2( - i j -e-
Naztt. 1. N., Member, Anademy 01'
(Doconn-A), klicho-rov, V. Fit
Andreycv, V. M. , 'o,tRal'.
S I, VY (It' i ne D iene. Con den .9,%LJ on ot 1-u-
At:etoxyvinyl- &-Cyclohexenr- With Malt-ic AId(ihv(If
(Starc-Achlinlya dipln--~ves:f v-114-nvatst;
*
c~~,c-~. 0- S,mloinovym szgid
Al-txllklaq
PUNODICINL: Dokla(4v hkadf-r-, ~ Nwik, vf~l IQ, 117.

R in flip ti 49 1 n k t)
f. voh-se
'A It, -!Il .o on f'r indivilylial
'
&-jid !i. its
!WP" xv- &3-r70 a, int.- 2-4%,c-a~-Uoxy lie
.'cul I Acurvair'n 4-19 . Vn the nas) s -i' the dato. nht"! nad
VOOkS ~ --jVII Lhrt. the ati-%-e-ri,-nLintien
~,f!. 8.-A rd. t .-,:I Y4- :utll* ig,o mt A o) F%fkl i 11 q t
V otte. ~.cinft gurat J i,n 1 3 und-r tht-pe uQn-ij t-' Ln,. Ott th"? wh-,
! r, , - (. n I. ! , s- I.be ru lo C f the p,:c jMU,. i:, L t w, ) r
1,ut t.,int. 3... o, ~,,, thw pr.,~,p(j thij C ttle ttqIU.: t I -e
;nniviwitil sind tnat: I t ~c-.onllfitns h ama, .1 quantity -of

trip fliav-~-Condenratiort of ;?~I-
Witti WA)ote- Aldphyrj.,
i romt, vi v ivti-cis-d-%I,,Att-xv-fLnhydride V irqf 2). 11 he fin F,
evidevit. ~hnt in fir. RI.Ad 3AP061, t'i cation of Lhe or vsiaIII--,-
mixture remnJnlrag atter lic-tration nf
'wetely SoAd 11 (4 it its Poubible t...3 ,-btT4,. 1!
Isuirterin tvarn.PVII-r:If-4-koto acid VI ( Mwi tt rig C(,-kf!f
I'lis, in tit; A
d t t: ' he r V11 - Tho, vim"
be! idirplated WjO. St !(j- yield f.r.)m th,~- Tirt-diint" it,'
n,-,-'d egrcnifji"~I(~n t)f 1-h P indivirivia!
17i. Trile waft .ind in,.Ii q'el th4l.
iWt,Ak wftL% nc-I ,j., e inliviiVift, ur th-it II-to
sap,.,njI'icaf.j.)n fjC tho ipn,:vtjtIv group ix
The I-tLkpr otu-ild ip-~ P--*rQCU.e (ref
~;;E-a-kefo rcin 'I.' ~iethvv
Lheir ty
tne proe,*' I t~i,lr
EngliMt to..ti -s (-#~T T s m , it r-
F,-,r thi % vurptse ayr.-c,. e--~nty-t; is-
xj was i,!i,i; -A I-v .(,vinhirr hq aftor the de- .rt,
Ca r-i Of fri- oomp,.:,~ an:, #0'!er ine treritvent -f ?h,

Trie Htqrq,)obemistry of drie Diene-Condensation of
Pvvipyl-Al -eyii1ohoxfne With MAinin Aldehyde
prod-act with diazometneup, cjS-gjycoj-Xj-eth*~r vus
isolatc-1. The oc)nfigurntir~n ol* the latter curreapon4s *,i t-110
liddition nf otimium IijIN from the aide cpr.O!,_,te tj tPe
oarbOYY'L grOlipR 'j'j;rtjjye To the %xial coaiticn it t.hP
tortiory hydroxvI vv,,,,v itom be
capable 4 dO.V01.4..11)n 'on '.6il"IlIg I'-fl,
slid yt-aidpol I'llf.
As "%r Pit Lw;jt!h ii -;Yr-f-rj~O i-n -7'. !r..,rvMa#AIy
it t ii -1 f q r. Y'?v a t' it C 7 q
4 1 t1, n n f t it - -y mumt -tie sttittj -.hht the vot-
ether produced .- inl,r n ,4% i,h., mF,-;Fi
prc.ditet real ''v r( Fen4 rP r r,- p_vv - ~: ! ,,- c :,n rxi ! i i
IfttIt-r in nutf! ~-i -nt)'viin q,,ie :,,cnf 1 vinn! Icn (I the
-P ar.1 ~ ,A Ai -!tht-r VYI
.(.rVigu2 _itn f,f
-. F, u -j: rp. An -:v vt -,Lri-:nt,i t r~%;- 9
the u f!'Ja I fin U. fj~ firt 0!,
wit: ch stre

.,.-hr-mi at ry of the
A Cetuvvv I tIY I- nticke- Vi I It, A Ile hvlq
~--N!IAT),-M: Instilut ortegnI.-hplio c
y 14
Ak4domli nbuk S511' III:' t to for OrRsn- rhp(ui!-v~,
to
N, P. Z*llTskiy A,~
-1TPM---7PED- Dc..,ember 21. 19W

li.(q - I

KUCHEROV, V. F.
fz~
G. M. Segall and V. F. Kucherovs "Stereochomiatry of the Oxidat'on o 4-
Octaline Carboxylic Acids."
report presented at the Symposium on Concepts of Conformation in Organic
Chemistry which took place in Hoacow at the IOKh AN SSSR (Institute of Organic
Chemistry, AS USSR) from September 30 to October 2, 1958.
Izvestiya Akademii nauk SSSR) Otdeleniye khimicheskikh, 1959j No. 3, 561-564.

KUCHMOV, V. F.
V. M. Andreyev and V. F. Kucher V., "Synthesis and Configuration of All
Poseible Isomers of 3,4-Dimethyl-,69 -Octaline Carboxylic Acids."
report presented at the Symposium on Concepts of Conformation in Organic
Chemistry which took place in Moscow at the IOKh AN SSSR (Institute of Oreanic
Chenistry, AS USSR) from September 30 to October 21 1958.
Izvestiya Akademii nauk SSSRj Otdeleniyo Wmicheskikh nauk,, 1959p No. 3p 561-564.

IWILER~Q'I V. F. (ICKh AS USSR, Moscow)
V. F. Kucherov and N. Ya. Grigorlyeva; 11 Application of the Principles of
Conformational Analysis for Proving the ConfigurAtion of Isomers of 3-Acetov
Cyclohexane-1,2,-dicarboxylic Acids."
report presented at the Symposium on Concepts of Conformation in Orranic
Chemistry which took place in Moscow at the I0Kh AN SSSH, (Institute of OrEanic
Chemistry, AS USSR) from September 30 to October 2j 1958,
Isvestiya Akademii nauk SSSR, Otdeleniye khimicheskikh nauk, 1959, No. 3, 561-564.

50)
AUTHORS: Kucherov, V. F., Segall, G. SOV/62-59-4-17/42
'
ra-Z -ar-o
TITLE: Investigation in the Field of Storeochemi3try of the Cyclic
Compounds (Issledovaniye v oblasti stereokhimii toikliches)-ikh
so,yedinaniy). Communication 22. Stereochemistry of the 0xida-
tion of Syn- A4-Octalono-l-Carboxylic Acid and the Configu::a-
tion of the Products Thus Obtained (Soobahcheniye 22. Ster~io-
khimiya okisleniya sin-,64-oktalin-l-karbonovoy kisloty i k3n-
figuratsiya poluchennykh pri etom produktov)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdcleniye khi~.iicheskjkh
19599 fir 4, pp 673-681 (USSR)
ABSTRACT: In the present work the previously dezycribed ('10r 1) syll-e-
octaleno-l-carboxylic acid fT" was inve3tliEated. It vaj found
that the oxidation of thi3 aell aB wzll ar, its catalyzed iydro-
genation are sterically selective funl that orl,,,r a sinCle
crystalline oxide (11) is quantitati,/~A;( forned by the action
of peracetic acid in chlorofor7. This oxide gives with diisr,-
methane a liquid ester (III). The u-oxiae shows a strong tend-
Card 1/3 ency to lactonize. When subjoctell to the action of

Investigation in the Field of Stereoc~emistry o-.* thu,
Cyclic Compounds. Communication 22. StAreachumintry of the O.-.1-idation of
Syn-,d4-Octaleno-l-Carboxylic Acid and the Configuration of the Prodnnt5
Thus Obtained
hydrogen chloride in ether or mhen boiled in nethan,)] df.vps
the hydroxy-l-lactone (TV) in -. hiji jield. The latt~-,- loo
formed when the oxydole enter (Ili~ is bollad ir -`ox-ne
in the presence of sulphuric to-id. The conf~idernticon o-,' a
model of epimeric hydroxy-y-lactones nhows that '.-he cxif.1
hydroxyl group in hydroxy-y-lactonc (IV) is leap sbields,-d than
the equatorial group in hydroxy-y-l-actone (IX), in whict, the
lactone nucleus can exercis2 itz steric action. As in ap,,,,~-zunt
from the configuration of gyn-44-octaleno-1-carboxylic acid M,
ito oxidation vith osmic aciO anhydride and with peracrv!~,,
acid can take place only fron the aide opro5ite to tht; o',~ilclded
axial carboxyl group. Owing to the ciB-hydroxylation, cia-
glycol of the cis-decalin series (XIV) is formed in this .-ase
and the eater (XV) of this compound is formed in a similar
manner by the oxidation of the syn-ester (XVI). The dehydration
of the cia-glycol (XIV) with p-tolueneoulphonic acid gives
Card 2/3 syn-c".s-4-ketodecali P-1-carboxylic acid (XVII), the este-r of

Investigation in the Field of Stereochemistry of the SOV/62-59-4-17/4','-
Cyclic Compounds. Communication 22. 3tereochomictry of the Oxidation of
Syn- 64-Octaleno-l-Carboxylic Acid and the Configuration of the Products
Thus Obtained
which is also formed by the dehydration of cis-glycol
ester (XV). The stereochemiatry of the oxidation of eyn- A4_
octaleno-1-carboxylic acid (1) with peracetic acid and osmic
acid anhydride can be demonstrated by molecular models
Page 676). The configuration and conformation of the a-ox-Lde
II) of the cis-glycol (XIV) and all their conversion producto
~
have been confirmed by infrared apectra, stercospecific rp.-
actiona and molecular modoln. There are 11 references, 5 of
which are Soviet.
ASSOCIATION: Institut organichenkoy khimii in. V. D. Zelinskogo Akademii
nauk SSSR (Institute of Or,-anic Chemistry imeni N. D.
Zolinskiy of the Academy of Scioncen, USSR)
SUBMITTED: July 10, 1957
Card 3/3

5(3)
AUTHORS: Kucherov, V. F., Ser,
al G. SOV/62-59-4-16/42
a ~za r o v
TITLE: Inventigation in the Field of the Stereochemistry of the Cyclic
Compounds (Issledovaniye v oblasti Btercokhimii tziklic%e9kikh
noyedineniy). Communication 23. ';tereochemistry of the Oxldn-
tion of Anti- A4_oc talano-l-Carboxylic Acid (Soob9hch,!niy(, 23.
Stereokhimiya okinleniya anti-,A4_ oktalin-l-karbonovoy ki.31oty)
PERIODICAL: Izvestiya Akademii nauk Otdeleniye khic-iicheakikh n,tok,
1959, TIr 4, pp 682-689 (USSR)
ABSTRACT: In the present work the oxidation of anti- 44__Oc tal eno-
oxylic acid (IV), in which tbe shioldint, action of the equato-
rial carboxyl ieads only to the trani-decalin syntem, win
investigated. In spite of a more widely opened double boid in
(IV) its oxidation is also 3terictlly selective Rnd forns a
single, individual a-oxide (V) in a yield of 30 %. When treated
with diazomethane this oxide rives a liquid oxide ester (VI).
owing to the preeence of the equatorial carbox~,.L a-cxid,2
cannot form lactones ani t.,hen boiled in aqueous dioxane in the
Card 1/4 presence of sulphuric acid gives the trann-Glycol (VII),

Investigation in the Field of the Stereochemistry of SOVI/62-59-4-18/42
the Cyclic Compounds. Communication 23. Stereochemistry of the Oxidation of
Anti-.A4_octaleno-l-Carboxylic Acid
The reaction has a similar course in the case of the oxidn
eater (VI), under formation of trans-glycol ester (VIII).
This is also obtained by treating (VII) with a diazomethane
eater solution. To prove the configuration of (VII) the de-
hydration of its eater (VIII) with p-toluene sulphonic acid
was investigated. It was found thatthis does not cause
lactonization wherean the previously described (Ref 4) etter
of trano-anti-4-ketodecalin-l-carboxylic acid (IX) is formed
in a good yield. This fact proves that the transglycol (vii)
contains a trans-decalin system with a diaxial distribut'-on
of the hydroxyl groups at C 4 and C, 0 and the carboxyl at C
in an equatorial position. This configuration confirms a' , 80
the a-configuration of the oxide cycle in the initial oxide M.
This configuration results from the addition of the oxygen from
the direction opposite to the equatorial carboxyl group. From
the same direction the hydroxylation of_(IV) with comic acid
anhydrideis effected. The resulting cis glycol (XII) wat
Card 2/4 found unable to lactonize. Its esterl also formed when the

Investigation in the Field of the Stereochemistry of sov/62-59-4-16/42
the Cyolic Compounds. Communication 23- Stereochemistry of the Oxidation of
Anti-,A4-octaleno-l-Carboxylic Acid
eater of anti-,44-octaleno-l-carboxylic acid (XIV) is reamated
with comic acid anhydride, formed upon dehydration th.7? c%tt,-r
of trano-anti-ketonic acid (IX). The cin-adduct (XYI) -w-te ob-
tained by condensing trans-1,2-dimethylbutadianc with mc'ha-
crylate at room temperature. Accordinj,, to the genoral Fl(,-,ic
laws applicable to diene synthesis, (XXI) must contain t!.ii
carboxyl group in axial position. For this reason the
cia-2,3-dimethyl-,63-cyclohexane-l-carboxylic acid (XXI*I'j
formed by the saponification of (XXI) forms easily the
I-lactone. A similar course has the oxidation of (1XIT) vkith
peracetic acid. The fact that the redultin a xide (XXI'i)
can easily form the hydroxy-y-lactone (XXV5 p;Zves clearly
the cie-configuration Pf the initial acid XXII) having the
carboxyl at C1 in axial position and the a-configuratior. of
the oxide (XXIV). There are 8 references, 6 of whi- are
Soviet,
Card 3/4

Investigation in the Field of the Stereochemistry of SOV/62-59-4-18/42
the Cyclic Compounds. Communication 23- Stereochomintry of the Oxidation of
Anti-,A4-Octaleno-l-Carboxylic Acid
ASSOCIATIOIT: Inatitut organicheskoy khimii im. N. D. Zelinskogo Akadenii
nauk SSSR (Institute of Organic Chemiatry imeni N. D.
Zelinskiy of the Academy of Sciences, USSR)
SUBMITTED: July 101 1957
Card 4/4

.10V
i i c In r, r ovv Gri, or'yovf, "n.
F
T IT L" - Tnvt~ntlgp-tlon.; in the Fie-I, tli- of Cyclic
Comrwindrq (1391edovani,ve v
t.; ik I! ch e a k soyo,~ i n,2ni.,, C,-r i ,.,.ni ion Di imu,
DiTio thy I Fvm a ratc. nn-' Con If ;i~ rritic-1 ',i:cts Obta I nod
;oobohcheniye 24. Di,?enovvy,i
s maleinovyn angifiridom it llr,,~tilfu virato,~.,
polychonnykh niduktov)
Akwlexiii n-,vil.- ;-hiTA--iiiokjAh nauk,
':r 5, pp
In Oilo work thu t1lione cnn~on3aticn of 1-acetox.,butadienn. zlth
anhydrHo riml limethl,rl N;-,ar~tte and the config-J.-ition
nn!! uatil)l trnw)fornntion of the pi-o3ijeti formed' ware f:-,Iv-,.n
thuritiqli inveitig-Airii. 1-Acofyj~,itrvlicne 7-mn'synthlsi2nd
to the Flaig fv~thwl. conlr3risf-Aion with -.'aloic
nznh.-Mride shoyied !3olectlvity with for.-IfIticri of the
.::i3-r,JS-Tlro hict (11 The confir-aratirn -.T,~s ~)roved by
Card 1/1" ijyliragena'tion awl lrtctoniz,~ticm. vVitn cond,?n'a,,!tion of

fmpps t Ir-. 1, ion:-, J.n t'--
of' co:-11r)"In"Is.
Field of the Sternochemintr.,t -SOV/62-59-5-14PO
Acom-willir.- lion 2,1. Diena Condr-nnationi of I-Acetoxy-
-nd nnil Config-aration of
tcc:r ')-o tfid i (.,n~ -rith fl-icth'-1 both i!3omars
~,r,~rc obtrinetIz trrmn-tr-ni -id tvinn-cia (XI" ind
X7), tw~ configlirtition of whic~i %,ri. nrovod b-., lth~'-ir C;talytic
!~y~,Ivo,,Ponrition, apponification, -nl thn observrtion of
.,,Olrculrr mod,)Is. The derivn~ivei of the cis-ci3 order and
tritria-cis orlor with nn FixiAl rtrrpn.~c-vmt of the acetoxy
','~ro,-Ip have P low stpbility. Tht,.v vi.)r,nr.-.te rxf)tic acid with
cntp.lytic hy4rogenfltion, !%lk!,Iin- ;-Irmifin-J ion, ~nd hentin,,!
-;hjIr., various ncitic nra lormod.
7he iaomeric coripounJ7 Of UIC crdcr rith. the
;~fpirtorlr.lly irranged -,re wfflcinntly ritablo
-3o V-T. 3o-ic of thni--.- Nbtnin.'. r a
:~ (I Tit n
Pri oo-jll' be
(011t of four thooroticall'- ~"C-
nynt!),ii7,~1 I,y !Tionni of dio-m
r og, ';Ii-)Y! -nd ;, thorov~'trli
iao- ,Ha trpnn-~-ox, -j-~Iicrrbox- lie c

Mic Field Of the
Cyc"c Co"nc Auctox~r-
d in,.~ '7 L t ri D im 9 t
tho Pro !.1!- 7, 'Aan
I T T
Uard V;

5 (3)
MIMS: Kucherov, V. F,, Andreyev, V. X., SOV/62-59-6-17/36
TITLE: Investigations in the Field of Stereochemistry of Cyclic Com-
pounds (Inaledoyaniya v oblasti zterookhimii taiklicheskikh
soyedineniy). Communication 25. The Condensation of Trans-192-
dimethylbutadione With Naleic Anhydride Synthesis and Configu-
ration of Your Isomers of the 3,4-dimet~yl-64-cyclohex&ne-ip2-
dicarbmViio Acid (Soobehoheniye 25- londensatsiya trana-lt2-
dimetilbutadiyana a maleinovym angidridom, Sintez i konfigura-
taiya chetyrekh izomerov 3,4-dimetil-A4-taikl'ogeksen-1,2-di-
karbonovoy kisloty)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1959, Nr 6, PP 1058 - 1067 (USSR)
ABSTRACT: The synthesis of the diene condensation (see title) which with
stereochemical selection forma the cis-cia-configuration (is')
was investigated. Up to now only the oia-cia-configuration
could be obtained. By further heating and in the presence of'
diethylaniline (IV) may be transformed into the isomeric cia-
Card 1/4 -trans-anhydride (VII). By means of saponification (VII) may

,Investigations in the Field of Stereochemistry of -BOV/62-59-6-17/36
Cyclic Compounds. Communication 25. The Condensation
of Trans-1,2-dimethylbutadione With Maleic Anhydride. Synthesis and Confiju-
ration of Four Isomers of the 3,4-dimethyl-,A4_cyclohexane-192-dicarbmaL, Acid
be transformed into the diaxially arranged carboxylic acid
(Vill'. The epimeric acid (V) corresponds to (VIII)l %he two
latter ones form the corresponding diesters (VI and IX). In
aqueous methanol (VI) could be transformed into a cis-cis-
diester which by the action of sodium methylate isomerizes to
the trans-tTan8-3,4-dimethyl-A4 rbzQM! axid
-cyclo-hexane-1,2-dica &
(XI). The last possible spatial isomer, the trans-cis-3,4-d-~-
methyl-A4-cyclohexane-I 9 2-dicarbAOIZ acid (XIV), is formed in
an analogous way. Thus, all four spatial isomers which are pos-
sible were obtaineds
M -Cooii~e~ (Vill) :COOH~e~ (XI)_QCOOH'e~
COOH a COOH~e
~CH;?H CH;Q COOH a CH 3 CH
3(e) 3(a) 3(e)
Card 2/4 melting point 173 0 melting point 161 0 melting point 150c)

Investigations in the Field of Stereochemistry of BOV/62-59-6-IT/36
Cyclic Compounds. Communication 25. The Condensation
of Tran8-1,2-dimethylbutadiene With Maleic Anhydride. Synthesis and Confij-,u-
ration of ?our Isomers of the 3,4-dimethyl-,64 -cyclohexane-1 2-dicarbagmc loid
(XIV) COOH(e)
CH () -COOH(e)
3 'C11 3(a)
melting point 1050
The existing configuration was determined by means of lacteni-
zation of the different compounds. When studying the spatiil
orientation of the lactonization it could be observed that with
the isomeric cis-trans- and trans-cis-aoids (VII) and (XIV'
also conversion forms take part, which are caused by repeaiad
isomerization of the cyclohexane ring. COOH(a)
H CH 3 LH
(e)HOOC- 6 1 1 ' 'I
.A (e)CH3 ~4
H- -COOH(q) H
_(a V.
Card 3/4 C3(a) XIV 001i(a) XIV(a)