SCIENTIFIC ABSTRACT PETROV, A.A. - PETROV, A.A.
Document Type:
Collection:
Document Number (FOIA) /ESDN (CREST):
CIA-RDP86-00513R001240410012-6
Release Decision:
RIF
Original Classification:
S
Document Page Count:
100
Document Creation Date:
November 2, 2016
Document Release Date:
July 19, 2001
Sequence Number:
12
Case Number:
Publication Date:
December 31, 1967
Content Type:
SCIENTIFIC ABSTRACT
File:
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v -a t- k"t f! t re A
u fth~ r o I il 1 t t r V t. V F;
a ru acetj le!.e b _i i It i f r t r - ,i, : , t
t i w -t t "'.9 ) :. T. . . -I - : : . ! , - : , . . , . - I I -
t 1 ~ .1 j r,: er ):. .- :- " :. - .. I -, : , , . - - " - -~ I , , .
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kuTHDRS. Potr-v, A. A. S,;1. K.- . 7. 3-1-1', 17
'T yak "V 1
TIT'~E. Ar i s 'Di s,~,tss i ~i pc rya~'e-.O,
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PERICDICAL. znl~rr-l"
(uss.,
ABSTRACT~ Th;~ 'ata I~f A'n r- I -a r: t,~ n 4 4 a - T' 1
t iF aryl ized with diazc. sr-I te -,ril y on tt,e
t~ .y I -ne ~ n~ I ave beer -~~nflrmed i n t r4- - - n t 1 y pu b 1
rt :.f A. V .)'nbr.)v.3kiy " Ref Th~ ex,lus ivelj -.1aim-
e I ',--aff ~'- irtti )7-L c)f zhiortne and aryl in this ra diva pr-,:-
ess Spem'.1 to the aalnf)rs :,,- t qu: te pr-A)aE.- . The frequent I.,
repeated analysis undF,,r :~-ndt.,.rna pr--csed by D)m trcvsk,.y
eltlowo-', that the r , .-- c.-)n,: ',,isiun -)f - is a-ith ,~r wlth re-
gar,l t,,, t~ie ch,ira,,ts!.- -f ct. r,,(LryI1 at I ,n if v inyl ucptilene
d,i,e,g n-11 )rreaij:)r:,! ',. : -eal ty . In evf~rj :ass,~ t~~e - var t ' ')V.
takr-a n1e.- formati c.-i -)f somewhat varjin'~ , b -,t always
Card 1/3 1-.iantiLies cf '117 all ajlu~tq)-
The Articl,7 13 open f - ~is
of th n CwLrsi- to r o f 17h I(, r,a-r Y t Y en-
Th o a -i t I , ) r!j i,a r, h i s v ri I h P La8 i a f tt,e knalyses
of infrared s~-trd f t~.4- 'n addition t--) t~,e fr-~,Iuen-
- i es ~, ' trt, A ~etj ' ;~ne 6:-- %hp ait z tra ~(,r. taired '-F, ttle f~ nal
phaeo an intersive freq,,.~-~ra j which -.u1 d only be att rbutf, !
t~, the u! ivne ,r-kij f '-I , t mpuiin i rt,I(.r--)aryltAt1 n
p r,j J,i,, 1, p ~ f ~ h e -1 1 n y I a o'jivne rJaIr, ',r. very gma,'!
quantities als, :i t,!~ i - 4 19 ~m- r t i- I .? n a e me r ' 11 1 . b e -
-huse ~ ; ~ , t, -, rr t? ,- 7 r ar, C (. I ~ - - El shows
a 9 ma 11 , ti ~ x f) - I.- 1 3 S I th ro--~ CII
Ac c o rd 1 rij~ Dom I r a k 1 5 rPT-rt phenyl vinyl acetylene tc
wh i - h 2 01,1~ a I I e rt e - h I , r -i e 1 Ej admixe,i, ~q -,bta,,ne,l a! the le-
hy1r, )f -ril ~rrjarjl;t! cn i,-., Jucts f '.he vin,,:
A---.)r,Iin6!y th . 3 1 erie h' -rllp cnrittiins a i Y~
-89 M( h,- a - e t y I e r1 e - h I -- r ~ ie I
r(, I L~ .1 c- r - p n j t i-n- ~ ~ ~, p m - t h , i , f 3
R ~ f , rma '.,.3 ; ~ '.,.ef w,,s us x~n I t~ is rearti-,n was
r, i ed ty i p a r t a: i, r (. pa rvy -F r f , rig and t t. p f -, rma t i n ') f
a m I x t U f a i x i ma 11 an i V 7?.o c n o r i i e
s m i x z-
Card 213
The krticle j.s -;pen f r )I,
of the Character f t f A
l'-L.nj it suol -vi. I e r,
owt -n jheryl -vine I -i ~,tylone
a i n P 4 ;k I e t, ir- nal -nl~ri If- V Tt.
u ~ t i -, r,I a- t h
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TITLE: Investigations in t,'.e Fiel.1 )f ~i. - e i*; a
v obla::ti sr),,r~ t 1 7,:- 1 1 1
Ace ty lenes 7i 1 t1, ` en-- -)y1 ~~-l rc pe r,)x~ -e
v in i I ~kl k i i -itso t i I (,;~ v :, i(i rc): elle',,. i:, iu e.,
P~--'RIOLICAL: Zl.urnal -)b,,; c: ey e,v.imii, V D 1 "'r 7. 1-
AK:TRACT In the paper3 -,f ~; ome .-,. t! - r!i *.a f 1 t a., n t
the c,L.,ic of ox i,.;Lt i -)r, () f i i:~y I L.,e t~ 1.1, - - ir' :.!7 *1, :
hyd r o -) e r -) x i,! es o a f !'i 1 i t~i nf x- e.. f. r ~ ..re
the etYylene . dor f ~) r i ~:. -) f a,-- e t- e:i e x 1. e!-, 0.'.
In the above papers -)al~ c (I e:-.e
hyr!rocarhoris were ined 1, e ):, e,! e r r 1 f!,!
ox: d i ze 'J.o v ii~Lj I P. t~ 1 - i y I e t u:i w
ben zoy I 1-y - - ),,). - - ) x i L O,o r., - -.; ~
i n t e ru ~ t i n ~ t -) f jL. i,: t r. o, L 'r -!~I!
ex ,perimen,i.,4: .-pr Pe r 'I
a 1 ky I c e tj i 0:, Us ti, o r 1 r i ii s 0 r-, , a 8 e o I , it', A
1, r om r in s i i. -u L t e r -i -) t e rm t the -, e; Lr ;,)f, )I t!.e I Lt'-?.'-
Ca.rd 1P froci Jibr-:%idet- h
Invest igat i ons i% %he I-'iel-4 f
C I. Uxid at ion of V i il'K.) r -,c r e
r)f ox-l.,,ti)n f --;, ) x
111. e -i ~ r i y 1 e t11 ice, ty e -e 1 Ile i 3
cons t -Ln t!: :,,e Lr e,: t lz f !.o 7 Z,
wh i ~~ ~. -I ~i ~- b t a : rL e, I e -tr e r 'b a~~n., r :i
,-et ..ore cert L.:..ty ~l -, it tr
Lice ere -)y e~;
,) b t,-. i,, i e 2h D,~,l e ~th.lt i:. e Q, eX
2he spectr,~m -)f t!-i e -) x i 4 et -Ji n e ril e j - -
carbor, differed :r) ~ 0.e -~-i-:.e )xi.!e r
bromhydrir, -).- , y b., L~,Q of ) f
mean iritun'sity ( ijrure). Ti~, fru-zenc~, o--: i:. t%e
npectr-,m of the liene )xie:; ire ~)lt -i e~
way. On the wl.olle the -)f 1.1,e ilnyl
and' the ii!.yl ell.yl acet iene .re i
re.,u I t.,3 )f the i; jectrr)sc,).- ic inve.,:tit~ it v":.
the cane of vi,,iyl ethyl t--,e uf'!- i it
the oxidation ,,.-ith t)on.-.oyl hj !rj!,er xi~e : ::-. L LK PS
p lace )r, e' :i . or.e b nd . I :i th e ~,ase )f i i i.,1
%cet,-'ene it C~Ln ~e !,-Ud with. resemr-Al )r- j z
Card 2/3 urient-Ai-)ri re,! e r e LLr e
Investieritions i:, 1 Y. e P - (. - . , f
U'I. Oxidation o I" Vir,~, 1 A ,:yl Art! ty . ur.e. N i tl~ r 0 e i x e
4 f '7hiCl. Lre . viet.
i,, loci,,,,rI,')N enin -r dsk iy te~hr, -)I -),-J che,~,. i. l., i t 0 ~ I I
1. e n in, - r 0 '1" f - c h ri c ~, 1 1s t -- t,~i t e Ir I
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Lnvest i#Kati oGs in the Fie I ; f e
C11. On the Directir,:i -,f ",,dr,,ti i. -;f Vi:,,
ketones vias 'let, heir
infrared spectra (Fi,~ure) u Iieario, of J)_~, ic 1 e 1
as by inve,,;Ligitti in If Uie N Lt~17 '.ted t!t ner
by hpirovewiti,),i. ~~,e coi,3t L;Ao irid infr,ir,~d c c t:- f
sy:i thes ized me tLy 1- - ro, en., e th-, I- , r j. I ~id,: pr r ~,; o,i,
keto!~eo -ire c, osely rebL ted t ~ 'Y.,)!-e i,i vk?rl ir, A I iC Al D,12
:~e f 3 -ill 2pe_-tr,i tlie -r-)Ljpin,- L pr )ven
fre,uerxies ,:i t,~e ran -e of m- . 1: 1
by the Tl-
h~~Iro,,;enation of all liy~raim ~..'oducts )ver P,11,,
led to the Alkyl pro-en~'l ketones described in :.u~lic iti-i,s
(Ref 12). T!,e afliliation rate -)f water lecre,i~;eii t~e
enlarE7ement of the nydro,.~rLrbor, r;idi cal. -- i~--~. c iuse.i t:.-.' t,~e
re,cti)n be carr.4ed out it :.e.*in.~. '7re -~_jmer )f ~f i_'-, ~tiz)n
of viater U1 4. ILI C 4101 U t 1 0 7 L"Ik.~' I ~ce ty le e-.- r- .a r.,-
to refer"11ce 1,1 toev -,nt -,rvov;,,,YA to ! !,o :j, in or,
af f i I iat im of !.~j 1 ro~ren ~.d es , w~, i ch i:. .'y ~) if, e ):, tf f t
th it * !~e.- e z-e a~- i on s tak e -ice d i f f e:-en'. 1, ere Lrt?
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Inv es tigLiti-)ro i:. t:,,e .~ ie ~ : ) f, , --) r, ~ .., I,.,;: ., t, .:, . I .. I - . - :. ,
CII. On the -'. -recti -)r, ) I ra * i ,, " '11[Q I :e . . ,
~~ , tj . UO
A.) S 0 C I A'~, I ON : Lerii;,6r-~dsiij te:0.%,)l 1. ~ :, - ~ , , *, .1 . . :1, e n 1 1, - f'. _. .- *~ ,
( L e n i ii~,- - t,! ~' V ';.. rl I " -). - 1 " 'I . I . 3 t I '. ~ *, Ll L.' . , ' . I . ; :, q ') i e *
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of to t~~,e cl. ~1,:e lene wi t!.-)U t ie'~ j lu-1
t'.e t j
.~cto :(-f!7 4). "he -u t Y, r.
iliacetylene a,~ s 'Aie 7i,.:ethyl 111 -1, t ".y I Ix. e
:ive the tert.,,:r-, -.-,e t r-~ ~'.ure -2
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infrared s e~:tram 'ercles A' t~_e
gro-.pizie 3x,~ f and a.;.d t'.e !'r _~encie- -,f e
nearly aboent. There Lr-~ .1 refe-2nCe'!, , f i C.,
ASSOCIATI')N: Lenini;rad~;?id- te.-hnr)!,),,i-he:`--.:L, ii .-tilut i-erii
(-'eningrad Tec?nolo.,:ical _'.-,:-.t.tute i ef,i
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rrt--sp r,ds t,~ that obtained by t~.~ r9
exactiy a I- 11,er instructions, hGwever i s y I ! . I
, 9 "IS 1 o r alL 9 m it er" trar. tnat ment',oried ri r--, t.
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LTL;-,t L-A t, r t~, the i t r . 6l. t r, e H,, G r a i. r r f :.3,
!,,an 1y Subs t i t it -d A-~-*Ly I !.Us
P z. R 1 ~ 1, ~--'A 1, Z h , r r. a o b s 1~ c El K ~, i 1 r
A35THACT: The monus aos t i t it ed ac, ti Y~c- t,y uroca rbons
a I k e ny I a c ~. ty ' . e r, e s , r e 9 11 t i r. ::. tI :.j 1 -a I& -! I - r a Ix trj 1
ket on, s only w f,er ejdra t ed under t ~,e rea C t Col.
sugeested by K~cner-v (Rtfs 1-5) . Ac --, rc.1 1.6 v v -a
acetylenes should result ir, alk 1-vinyi -tones, hcwcver,
ad- water ,uite irregularly undtr tne ',r-.ation -f ai(y' r
p,ar,y I k e t o n e-s . un t n e b as i,~; j f t t,t!,: r t t , c a 1 c r) r,F i ! - : -a t I s
order of hjurat iur. can i; ~ t!~er bt- uxt- 1,i , , I 1~o * t
of wat er nor by pola rizat ior, Df the mili,cu I eB c.!* v -~ r,,, I--I I r-.~j
ac t, ty 1 eziL und er t he i rj fl ae n ~~e c, f ra d i ca Is . To f [A t!.E- ca
for the hydration a, r. ct ion of* vir.~-I - and ~iiv- a----t
the d i rect i on n -ih I c~" wa t er i a -i c
alkjl acEtyl~-I'es %as invest igTit,a by K..ic! 'rov Is
Comparable data on t~.ese prcblt-as ~.av,~ r.,' ye, Iea't h,
Card 1112 in publications. The cu,:.positJ1Ln Qf tf.e la:xt-r,s Aqj
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i ia i i ',iy- L i 1A
kERIODICAL: Dukladj Ahademi i r, ii u,, AF
p
i,BLMu~CT Tl'ere are U."Ij lew data ltvi"IcIlb.tl It
C ,)M,:' .1 . , I f 1 1 ttl I um - - r ~' a:" ! c um -:.1 9 t t' '
bLnds Ref!3 ., . V nor. e r i 1 :' U ~A
cin,Ly rjy ir,eEj r),e a c *. 'El , : -
substituted firial :arbcr, atom. 1 1 t r. 1,-AiL - r
act Lq,n lefines and diuofines.a to"M. l- c j
Huwever. :3 u L t ar. c e 8 c ar. 'b e i s 1 a t 1"r - :r. e
after t~,e h., cr r t:, e tr-e,*':;'-
FA.-:0rd I ne, t' t 1142 1 F :-Ill i !-'q C( r["'.Li;,on,!
I n t 11 1! e it f~' f I , '~ I I f. '_ - c.. . , . I . :
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Card 1/5 c,, r - j , a ! . r t ! e r 1, -f ~ .- ::_~ r -, a ~ f. ' I
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uosc r~ t , or. t 3 a~'-! i
fre i uer.--- i e s at - c m T n t: a E3 t - ir. te ri t , o r. e dr, v
m( at likeV to be f'nrmed ny t1v i a um e r i ~,A t i k, n ( !t ri A I I e sy m t #--,L
i n t e i j m e r . , 1, e a b u v e - .1 1 acuseijd react i(,,i i!j ki ,.,-,w
m,i t L ~! f ~ r (, ~ u i-, i i,F, t loc i e Fi z3 t n c~ s!3 i o I eai,d i i. a '. ~,; ae,i
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I,AE3ENTED: December A Elde- 1 a~--
SUBMITTEDt Ncvember ~4
Card 5/ 3
5 (2,3)
AUTHORS: Petrov, A. A., Kormer, V A SGV/2(~- 1 2,~ 7-
TITLE: On the Addition of Lithium Diethyl and Lithiiii Dibuty] Am,d-
to Vinyl Acetylene and to Vinyl Alkyl Acetylenes (Q pri3nyp
dinenii litiy4ietil- i litiydibutilamidov k vinilatsetilenu
i vinilalkilateetilenaml
PERIODICAL: Doklady Akademii nauk SgSR, 1951, Vol 126. Nr F,, pp 1~78 "-91
(USSR)
ABSTRACT: Cnly few data are available in publications zon,7erninp the
ject mentioned in the title (Pefs 1-3). in the present paper it
is proved that tne adducts of amines tdiethyl and dibutyl am-
ines) to vinyl acetylene hydrocarbons form by treating thp ad
dition products of the lithium dialkyl amides t-) theep qy,iro-
carbons with water. The mentioned alkyl diamides react at r,-.om
temperature and under n-)rmal pressure , 'This reaction :t;iE, ~.--*h
erto not been described. According to the riature of viny, t-e
tylene hydro(7arbon and tne amide various products form from th-
corre8pondinf~ reaction. Vinyl acetylen,- forms dmin.-s (.117 -with
an acetylene end group (in the case of diethyl amine with a 20<
yield) without any side processes. Besides polymers :12' ~'J-i
Card vinyl methyl acetylene produces mainly the dimer (IV with a
On the Addition of Lithium Diethyl and 411thlium
Dibutyl Amide to Vinyl Acetylene and to Yiny!
k1kyl Acetylenes
yield of approximately 4,Yxf. Aminee form :)nly in veT'Y I )w y-, -,Is
( 'l-% '~ they havo diffPrent structure &ccorlinz tr) thp nA*.ur-f
the amide. in the oase of the addition of lithium liethv, -r.
ide an amine frms with an acetylene end group V r,
of the lithium d1butyl amile an allenp amine 7 ;mp-lind V; i
formed (see scheme). VInyl ethyl acelylene fvrnishes allenp
amines of the typ- .'VI) with lithium dialKyl amid-e .1 r r r L~
The dimer amount Joes n,.t surpass 1 J~,"c . The st rur t-ire ' f t. r ~. a M
Ines was determined aojve ai: oy their infrFire-1. sper Ira F-~K
I ). I,ientit,~es with already knDwn 5ub9t,.inces w~-r- fr~uni -,r. '-hl~
connection (Ref 4~. Moreover, the qtr-~,tur- of the aminaq wag
determined by hydrogenation on -olloidal palladium ' P e f ' -In
the infrared spectrum of the timer of vinyl, methyt -A-,-~yIP7~~
the abeorptinn in the r,tnove of from 964 c,,D tha'. ttle
double bond is f,,rmo--d by a -CH-CH-- P,,r,)uF,. ',FIK A' -
cording to all these data the dimer may ~.e as~rifet form-,:&:
6-methyl-nonene-l-dii-ne ' 8 (VI,', The dimer -t ~ry: ethyl i !
Card 2/3 tylene has an anal-g'7'us structure. It is M-9t pr-)tat'le !~;i" the
On the Addition of Lithium Diethyl and Lithium 3 2 1 1, - ' 7 li,
Dibutyl. kmide to Vinyl Acetylene and to Vinyl Alkyl
Acetylenes
PRESENTED;
SUBMITTED
dimers form due to the addition of their metallization pr~,ducts
to vinyl acetylenes. In this connection the multiple bonds are
shifted to the end of the chain un,ter the effect of the lithl,,.n
dialkyl amides. Table I gives the constantq of the produced
substances. Thus, it was found that lithium dialkyl amides may
be added to the vinyl acetylenes similar to the lithium alkyls
the radical enters position 4 (Ref 7). In b,~th cases the reat--
ion probably takes place according to the radi-al mpchaniain.
There are I figure 2 tqtles, and ) references 4 of wh1rh ar~-
Soviet.
March 4, 1)5~, by B. A. Arbuzov, Academician
February t.
Card 3/3
5W
AUTHORSt Polyakova, A. A., i na, K.
Khmellnitskiy, R. A.
TITLEt Mass Spectra -Ind Stril-ture ~)f 71r,_--!_ A~-t.,If-n- 1ro-arbons
PERIODICALt Doklady Akttd~mii riau~ SSS:,,, 1'1,~'), Vul 1"'I, :;r
(USSR)
AB3TRACT: InvestiCations of rr~iatirns existing betweer. phyF-Cal
properties influencinj Aructtire and reactivity su~yly irita
for infrared spectra (!~ef 2), Tiaman 9pectra ('.'.-f 3), and dipol-,
moments (.;Ief 4). r.,esulte obtained from inve9tiCationn with the
US-1 mass spectrocrajj)~ fire rci,orted ',.ere. The rra3o sj,e~:'.ra )f
vinyl acetyl and of its threc. monomethyl do:-ivat1v-s ws-re ta~,n.
Results are specified ii, tablE 1. Maximum intpr.~_-ity is
exhibited by the molecular ion. 2he most intense split ions are
produced by the rupture of the C-H bond. Split ions .ro,!uced by
the rujiture of the C-C bond arf) not typical of thpse compounds.
Unlike I-iperylpno arid laoprvn~, t!tc- introducti,)n of a iw-thyl
radical decreases but little thr- stability o' 'he mcl-cular icn.
"he normal chain isomers difer from i3oproj-yl acetylt-ne 'r~- a
greater intenoity of the peak C H+-Ion)
Card 1/2 5 7
Mass Spectra and Structure of Vin~,! Acetylene H.,,drocarbons SOV/20-1 27-2-42"70
A striking fact is that the greatest stability is exhibIted
by those split ions which have ccnjugate bonds. It woull be
interestIng to compare these ~rolerties with data conc;~rriing
the kinetics of the ion reaclions of -7in,71 acetvlenes.
Unf ortunately , there are no s,;ch data avai I able i n publ i -at'~ one.
Thorp are 1 table and (, references, I of which are Sovi--~.
ASSOCIATION: Vsesoyuznyy institut po 1'~T-(-rrLbotke
nef t I i -az a I 10 11!,! 1--T%iY'-1 i W-u as tvi,nnogo zhi I koeo to F I i va
(All-Union Scientiric .'.-search :nat'-t,ite for Ts-troleu-n and ';as
RefininC n-d Irolucti'm of Synthotic Liquil Fu-~Is~
PRESE!""ED: March 110, 1""') A Arbuzci, A,-,idomiciin
SUBMI7TED: March 21, 111--1
Card 2/2
CC
AUTHORS. Petrov, A. A Kormer, V 5115 3/6o/oc ,,'c i,
BO I I /BG C I
TITLEs On the Addition of Lithium Alkyls or Divinyl Acetylene
PERIODICALi Izvestiya vysshikh u~,,hebnykh zavedeniy Kh1mIya i ktiml~~hoskaf4
tekhnolof.riya, 1960, Vol 3, Nr 1. pp 112-114 (USSR)
TEXT: Thi- authors, experiments showed that lithium alkyla readily red~t wit'.
divinyl acetylene, Industrial divinyl acetylene with small impurities of
acetylenyl divinyl and about 20% of xylene, lith-ium ethyl, 2 Isomeric lithi,..T,
butyls, and lithium amyl were used for this purpose With each of the I i thi um
alkyls mentioned divinyl acetylene could form 6 different adducts (1.2- 1 4
and 1,6-addition~ with triene- or enine groups. The authors, however, expected
that only vinyl-allene hydrocarbons would form on the basis of the rules
established before I CH ?-CH-CH=-C~CH-CH2-R (after treatin6 the adllirtt
with water), The acety enyl divinyl present as an admixture would not take ax.
active part in the formation of monomer products The experiments confirme,!
assumption. Only 1,3,4-triene hydrocarbons were formed. They contained only
traces of acetylene compounds The structure of the reaction products was
on the basis of their infrared and ultraviolet spectra as well as by hydrr,
genation to saturated hydrocarbons A normal structure of the hydiocarbOLS lSel
C 1 12
Card /
C, )(J ~, -1
On the Addition of Lithium Alkyls on Divinyl S/153/60/003/01/029/058
Acetylene B011/ .005
was proved in all cases, There were no fully conjugate trienes Table 1 presents
the constants of the vinyl allenes obtained for tho first time. Vinyl allenes
have much smaller refractive indices than 1,3,5-trionea. The figure (P 114) shows
the infrared spectra of trionesirecorded by an IKS-14 spectrophotometer The
spectra will be describeiand analyzed in a separate paper. There are I figure
2 tables, and 5 references, 4 of which are Soviet.
ASSOCILTION: Leningradskiy takhnologichaskiy institut im. Lensoveta; Kafedra
organicheskoy khimii (Leningrad Technological Institute imeni
Lensovet; Chair of Organic Chemistry)
SUBMITTEDt April 13, 1959
Card 212
83507
r,,,, L) .2 Z 0
C, L'
AT,T r(. v , P~ . A.
TIT LE V i riyl Acetfenr- arl
its Hono'r)F,3
3
S '07 60/0 C
P. 0 (1 4
B01
PFRIODICAL: UspPkhl kh:MI;. 1W)(J), pp.
TEXT: The present survey ~,,als with the methods of synthes',zing enir,
tydrocarbors and Tr-jpert ie.z. Before the Thirti eq, these compounig
had been Investigatec) on..v , ,. 1 ~'RefF. 1-16~. The majority of known
enin hydroca--no have oeen desrribed in tne course of the last twenty
~,ears. Table 2 shows their formulas and constants. Enin hydrocarbons -,r.
0,~ Pynthesizpd by various metnnds ; the most frequently used start ing
material is ar7etylene. Enin hydrocarbons can be 1 ) gyntnevized from
compounds with the same numofr of nydrocarbon atoms. The fnl!~-,winv mp t nc Js
- I (jn arc des~~ribed in this connection: nyrthes:7' rrrrr, n-al -gen
. Preparq!.
Jer,,vatives - Re's. e,. 7t el 20-4F4' , dehydration of Ficety~ene Fi.- r,-,
RP's. '0. '4, 4?-'0')' , s~-jarati, n r" alky! nypo?iaI(.,vPr , " a , t.,
I,ls ;Refq. 1 10. 114' , total methylation of unsaturatol amnpq
(Refs- 4- 9, 1 11) and spipclive hydrogenat ion of dia(-Ptyipries hZ
Card 114
11,3507
rij A rf t y Pno T(,- m- S ") ' 4
Ai 'Br%t 4
By r t Pe Q ! Z e f, n I
1 n h y I ro -Firb )r.,
p in. g r. j rr, r a r 7, at-m p n tr.
.w qi n 3 aro apr . i e 7 zj t ~r. a"(, o rr, y i r F~ r 1),
3 a n it o w r oriv i v f? q
T. v 14- n r, rl r py i n a ,I p p a tn ~jnsat-irttl e 'I r ea r,
m po u Ila st p q 7 h aK y t
o w r (-i r R efs
F, ri r, n.,,,d 7, r~ a rn s rc -r :T
g r. t Im ):r s t 2 r
r p 3 a r op r
a r o a D - r Rk3 C
m r r i - r
-T - n I t n .,,~re3tn ~i- mu i E, b nd ii , a npo 7 1 a y ~r a n u im
z t r 9t wr
r,
3
fD z a T% n e o n ovr--)u~ react r..,, m,
n m.,
qr b Y m ~ o u rA s 7, a ii oz r-
83507
'finy, Acetylene and Its 7 4
~io I ~06 4
mui tip I e bond s ar,? des cr i ced : tne ef ~P C t of Ox zing agents R- A
. 91) 9 8, " 4'~ - h:(d r o tr
78, enationVRefs. ?9, 1)?, IP 0 ,
addition of halogens (Refs. ~, ~q, ~Q, `~, 4", 4 , 46, 166,
d, I , (Refj. -,F11- 10i a-, i i r),
, -)n )~ ny1rogen Caps
r,.~ p c~ r, q,ogen acids and trpi r tstpri fPofs. 1 '017 - I.) i ad d
'I, ~L er, ai conois , arlds, ari p~.Pnols Refs . V)- TA I I o r.
jf u r - , ri i t ro ge n - n -).q pri r) ru 9
arJ s, icon c~,mFounds ~Rpf,3.
i Ii ~ i - n a t r. i er. w, t n er. r. p, 7 a r 1),, r) 1~ h f i ,ri . T.1 8 Vr 11 p C.OM: ~- jq p ,; rr, jj - t
Lth it oPtI vri es ( h i f f, Vi ! r - ~- r-, I i - it I ~i P e t, . ~r, rKlIrl I (rI
mpou n dvII s, fi4. i ") ., t) I. ') We r I I ., r i v a t iv n q - * , - , , ~ - r.
,;i rii do Ref'. ~7P~ , n i rk e 1 - q r b,) n.,,, I Re rr; . 1 7 '1 - '92 ~ , d i a, Ky.
R e ~ . I, ~ , a nd d i a z ) c ~ m,; o i n I s ' PP f 5 . 584- Some cases -i m r . Z
t 10 r, w i t n a s r, rt ,f th(- mu ~t,; I P ocnds aro AP.9cribed 'Refs. 10
, ;~ - ~ -3 1 , - 9 , " 4 14 1 1 HR , j L " ,
. j : 9, 90 Re f*3 . ' '4 1 -4 1 I-j I a i tr.
J m e r a tLon ani prlymeri za t ; ,n v ny FAce ty : onp and t s h m 9 , o g.?
' * ht hP add -, L-ion of f I u o r ry o I ? f i n -s and Refs. 4 1 5 - 4 ? ' w t r, t ri~
rm a I i n n of Tp ! P x z mp o u n(i s . Refs. 424-VO JescrDe tne t s t t j
enr riy1rn-en ty hal )Rpn.9 ani Refs,
u t i on by ma ta! and me t a; '. r, i d i . ~on-jp ripa t i -r. v i t n -a rr), r, m, -,,,n i
83507
r).11 ' Ar,,tyPnP ani t9 d i n 51 ? 4 'v, 0, o,,
W'l ~ Bof~4
tip ompvnq - r f 'I I , r, n P n i Fi e R p
'tr, we r ,q
M. ft 9 X j A
~armanov, K a v a ne r r K v r IK it
oT, r r K iY , S. A. V~irtanvar finJ 1 14 Na7 a r- v ri fr P r.
n~ -e arp ~ i,~tt c- 9 a r. Sr),,,p
A A T N e rl I T! I- r'i t " K K
n r gr Ri r, p m
~. - . . " t. ! .
"X . I I
C., -.. "- , , . . . . :
-J,-
. . : . A ". A
I j - I
I I .
-L .- .
I
: , :~ , A I -
':
, ~::; X I I
~ , ; I f "I -
"*Irfi -~
; .- I -
,%-- i, _-
F - ~ ~ G -1 , , ;, , , -
A : . - - * , "~
. .1 . . . . .
. I '. - I
3/079/60.,'05C '04
BOO 1,'BC) I
AUTHORS Petrov, A, A Razumova, N. A- ^,enusov, M L Yqk~v'-a
TITLE Exchange Reactions of Telomerslof Diene Hydrocarbons
Containing Chlorine I Reachons between Some Lcw T,' m-
of Dienel drocarbons and Azines-1
PERIONCAL Zhurnal -Ashchey kh.mi. , '9'-C. V,-, G N c, 4,
TEXT In -.ontinuation of the capers by the authors of the pre,3en,
R o f and the papers of Ref 2. it was f ) nter--,st tc a~' '; )w t
of 2 -ch"oro pentene- 3 to di eneR whi ch may h 1 sa be reVarde-i 8!; PI: Y
halogen derivatives to react with nucler,~hllls reagents, A
the primary and secondary &mines, Two types of compo--jrds wi tr j i
podition of the double bonds (A and B) may he expected to he f-r-
tr,is connection R
CHA - CH - CH - CH CH, - C - CH - CH.,
CH, NR'2 and
Card 1/3
3/079/60/0 5C, t4,'2
BOO 1 /BO 16
AUTHORS: Petrov, A. A,, Bunina-Krivorukova, L. I.
7
TITLE. Exchange Reactions of Telomeralof Diane Hydrocarbons
Containing Chlorine. II Reaction of 1-Chloro-l-met* I-,
I-Chloro-3,5-dimethyl-, and 1,3-Dichloro-5-methyl
octadione-2,6 Rith Sodium ;Lcetoacetic Eater
PERIODICAL. Zhurnal ob5hchey khiinii, 1960, Vol !C, No 4. p~ 116-1-116-
TEXT: In continuation of their previous paper (Ref. 1), the authors
described In the present one the above-ment~oned excnange reactions
are of intereat as intermediate stages in the synthesis of alcch~-,!s -~f
sesquiterpene series, thair homologs and analogs- From among the nu-Mpro'19
reactions of 9.1lyl halogen Jerivatives with sodium acetoacetic eater de-
scribed in publications those are important for the present inv1--StiFFi-
tion In which crotyl chloride, prenyl chloride, and 1,!-dichloro ',L'tene
take part since these ch'lorido8 rontain the aame atom 6rouping in eni
position as the telomera investigated previously b:~ the uuthorq i'l
chlorides mentioned yieldi?d ketoneslas end proiucts which contain r,.-
Card 1/3
Exchange Reactions of Talomers of Diene Hydro- S /0 7 9 / 6 0,10 3C e 0
carbons Containing Chlorinc- 11. Reaction of BOG I "BC 16
I-Chloro-5-methyl-, 1-Chlora-5,5-dimetrijl-, ani
1,3-Dichloro-5-methyl octadiene-2,6 With Sodium
icetoacetic Ester
vinyl group (Refs. 2-7) 2-Vethyl hepten-2-one-6 was obtained, ir.
special case, from prenyl chloride (Refs 2,~) The reactions -f
- 5 -m ot hy I -, 1 -chl oro- 3, 5 - d i me thy I -, ar. 1 1 , 5 - d i ch 1 oro - 5 -mt t hY I r. - t"t
diene-2,6 (telomers of 2-chloro pentene-3 with divinyl iscprenfw~
chloroprerie) with sodium acetoacetic ester showed in the lnfrar*,~'
investigated (Diagram) that also in this case ketones without vin~-~ 6r 1
occur as end prgducts (Table 1), Thus, isomeric ketones of th- t
CH CH-CR CH C0_CH,, which should be present in the case of a
2. 2- 2-
allyl rearrangement, could not be detected. The resultant ket-jr
colorless oils with peculiar, pleasant odor Three ketones, 4-m~,hi.
undecadiene-2,6-one-10, 4,6-dimethyl-undecadiene-2,6-ore-10, 'Ird ~ .!. r
-4-methyl-undecadiene-2,6-one-10 were lescribe! Therc- Eire I ` -r.
tables, and 8 references, ~ of which are Sov-iet,
ASSOCTITION- Leningradakly tekhnologicheakly in,4titut imeni LP_n:;-_---
'Leningrad Institute of Technology imeni Lensovet
Card 2/3
1410 0
AUTHORSt Petrov, A A., Porfir'yeva, Yu
TITLE: Investigations in the Field of
the Problem of ~he Direction of
Vinyl AcetyleneiHydrocarbons
PERIODICALi Zhurnal obahchey khimii, 1960,
S/07 6o/o50/05/09/074
B005YI3002
I , Yakovleva, r V
Conjugate Systems CXVII On
the Addition of Halogens to
Vol 30, No '~, pp 1441-1444
TEXT: The authors of the present paper describe their investigations
concerning the addition of chlorine and Iodine bromide to vinyl acetylene
and vinyl ethyl acetylene Iodine bromide lies between bromine and
iod1ne as to its reactivity and has a dipole moment of 0 4 Debye (Ref,
The structures of the addition products were determined by analyzing their
Infrared spectra. On the addition of chlorine to vinyl acetylene there
occurs a mixture of allene- and acetylene derivative with a low percent-
age of dichloride of butadiene. Chlorine therefore behaves in much the
same way an bromine in the reaction with vinyl acetylene, the only
difference being in that a larger amount of 5,4-addition prQdurt anc a
smaller amount of 1,2-addition product are obtained on a chl3rine ~sziiti~,n
Card 1/3
Investigations in the Field of Conjugate S/079
Systems CXVII, On the Problem of the Lirection B005/BO02
of the Addition of Halogens to Vinyl Acetylene
Hydrocarbons
than would be the case with bromine addition The nain product to result
on the chlorination of vinyl ethyl acetylene is the acetylene derivative
with a very small admixture of 1,3-diene derivative. Thus, chlorine
behaves here in much the same way as bromine. Unlike chlorine, iodine
bromide is preferably added to the triple bond in both hydrocarbons
under investigation Addition to the double bond occurs to a small extent,
while the corresponding allene derivatives are formed in an inconsider-
able amount Therefore, iodine bromide behaves in much the same way as
Iodine on the addition The procedures followed in the investigations
are described in an experimental part, Yields, boiling points, densities,
and refractive indices of the dihalide mixtures obtained are specified
along with the elementary per cent analyses- The characteristic fre-
quencies of the infrared spectra of the mixtures obtained are specified
as well, In all cases, the dihalides were isolated by the vacuum
distillation of the reaction products, since large amounts of hign-
boiling higher halides were also obtained on halogenization. To eliminate
the possibility of an error due to an isomerization of the reaction
Card 2/3
Investigations in the Field of Conjugate S/079/60/030/05,'09/074
Systems. CIVII. On the Problem of the Direction B005/BO02
of the Addition of Halogens to Vinyl Acetylene
Hydrocarbons
products during distillation, the infrared spectra of the crude reaction
products were investigated as well, In all cases, these spectra con-
tained the characteristic bands of such dihalides as were afterwards
isolated from the mixtures, A figure shows the infrared spectra of the
4 mixtures of dihalogen hydrocarbons obtained. There are 1 fig-ure and
7 Soviet references,,
ASSOCIATION: Leningradskly tekbnologicheakiy Institut imeni Lensoveta
(Leningrad Institute of Technology imeni Lensovet)
SUBMITTEDt April 22, 1959
Card 5/3
S/07 60/030/05/10/074
Y
S; B002
B005
AUTHORSt Chelpanova, h. F., Nemirovakiy , V D., PVtrov, A, A.,
Takovleva, T V.
TITM Investigations in the Field of Conjugate Systems. CXVIII. 01
the Direction of the Addition of Bromine to Vinyl Acetylene
Ketonepq
PERIODICALt Zhurnal obahchey khimii, 1960, Vol 30, No. 5, PP. 1445-1450
TEM By way of introduction the authors offer a brief survey of publi-
cations concerning the rules governing the addition of bromine to vinyl
acetylene hydrocarbons (Refs. 1-4) and to derivqtives of vinyl acetylene
hydrocarbons (Refs, 5, 6) In the paper under review, they describe the
results of their investigations on the direction of bromine additi-n to
vinyl acetylene ketones of the following two types (I) and (11):
CH 3- CC-CH-CH-C=-CH (1) R-CO-CZC-CH-CH2 (11)
(IIa) R - CH3 (IIb) R. C2H 5
(IIc) R- n-C H
7
Card 1/4
Investi#,-ations in tne Fieid ui' -.onjugate S/07 6o/o3O/O5,'10/074
Systems. CXVIII. On the Direc'tion of tne B005YB002
Addition of Bromine to Vinyl Acetylene Ketones
The structures of the addition products were defined by the analysis of
their infrared spectra Spectroscopic measurements were made on a
spectrophotometer of type OKC-14 (IKS--14) . The characteristic frequencies
of the two compound types (1) and (II) are given. To determine the
direction of the bromine addition to the ketones mentioned, the infra-
red spectra of the solutions of these ketones in carbon tatrEchloride were
compared with the spectra of solutions of bromination products in the
same solvent. Since the bromides were not isolated from the reaction
mixtures, the results supplied refer to the original products of
bromination, On the bromination of ketone (I) with the equimolar amount
of bromine, this is preferably added to the triple bond At the same
time there also occurs an addition to the double bond, giving rise to a
non-conjugate system The 1,4-addition which is characteristir of the
respective hydrocarbon, dOOB not occur in the case of the ,Pt~,ro On tne
bromInRtIon of ketonen (11a), (11b), tind (Ilc), the additl-r I.,) 'he triplo
burd )ir.i the addition to t-he loitlo bord proceed t,-i7etf(-r ~ ' . ' . ' ' - *
ioes not occur here either. The dihromides of ketone (1) CiDUIJ -. t
isolate!, since a decomposition took place an distillati,~n Df th-?
.ard 2/4
Investigations in the Field of Conjugate Z/079 '6G/O ~j_74
Systems CXVIII On the Diructi r, of tt.v BOO 57BU 2
Addition of Bromine to Vinyl Aoetylene Ketones
reaction mixture The dibromideF of ketone (Ila) were isolqted fro7
reaction mixture. The analysis of their infrared spectrum, shown in
Fig. 4, confirmed the above statement concerning the direction of
bromine addition. It may be stated in conclusion that vinyl acetylene
ketones add bromine to a considerably less selective extent thar. the
respective hydrocarbons Another characteristic feature is the com-
plete absence of 1,4-addition, as well as the relatively high reacti.,n
rate of bromine addition The otherwise low reactivity of tho trillol
bond is increased by the carbanyl group It proceeds therefrom that the
additinn of bromine to the ketones mentioned is probably a nurloophill-
reaction (cf also Refs 9-11) An experimental part contairs Jftta on
production, along with main physical data and the characteristic infrd-
red frequencies of the 4 ketones investigated The reactirn conditi,rs
in bromination and the physical data of the isolated mixture of the
dibromides of the ketone (Ila) are specified as well Figs i and ' b:,(-h
'hP infrared spectra of the 4 ketones investigated and the prod,ictp ~f
-.helr bromination There are 4 figures and 15 referencesi 9 Soviet
z English, and 2 German
Card 3/4
Invootigations in the Yinid of onjugate S/079 60/550/0L,/10/074
Systems. CXVIII. On the Direction of the
B005,BOO2
Addition of Bromine to Vinyl Acetylene Ketones
ASSOCIATIONi Leningradakiy takhnologiche8kiy institut imeni. Lensoveta
(Leningrad Institute of Technology imen~ Lensovet)
SUBMITTEDs May 25, 1959
Card 4/4
3/079 '60/050/0~/'l 1/074
zoo
-51 B005~B002
AUTHORSt Petrov,A A , Kolyaekina , Z-N.
1
TITLEt Reaction s of Chlorine-co of Diene Hydro-
ntaining Telomer.
carbons. III Production of Lldehydes and Ketones From the
Products of the Addition of Tertiary Butyl Chloride to
Diviny17 and Chloroprene 7
PERIODICALi Zhurnal obah chey khimii, 1960, Vol 50, No. 5. pp. 1450-1454
TEXT: The investigation of the telowerization reaction of diene hydro-
carbons with saturated alkyl halides1showed that only tertiary alkyl
halides secure good yields of monomeric addition compounds of the type
R-C 4H6- C1 (Ref. 1). The, authors of the preigent paper investigated the
conversion of these halogen-containing addition products in unsaturated
aldehydes and ketones with a quaternary carbon atom The scheme of this
reaction is given. On the addition of tertiary butyl chloride to butadiene
there arises 1-chloro-5,5-dimethyl-herene-2. The structure of this pro-
duct was clearly defined by analyzing Itu infrared spectru~n (Fig, 1).
Card 1/4
Reactions of Chlorine-containing Telomers of 5/079/60/030/05,11,"074
Diene Hydrocarbons, III Production of B0051B002
Aldehydes and Ketones From the Products of the
Addition of Tertiary Butyl Chloride to Divinyl
and Chloroprene
The product of the addition of tertiary butyl chloride to chloroprene had
already been obtained at the authors' laboratory in 1953, but the data
concerning this compound had not been published. The analysis of the
infrared spectrum (Fig. 1) showed that this product is 1,3-dichloro-5,5-
dimethyl hexene-2. The two unsaturated chlorides mentioned were convert-
ed into the corresponding unsaturated aldehydes by the aid of Sommle's
reaction (Ref. 3). In this manner, 5,5-dimethyl hexene-2-al W was ob-
tained from 1-chloro-5,5-dimethvl-hexene-2, and 3-chloro-5,5-dimethyl
hexene-2-al (II) was obtained from 1,3-dichloro-5,5-dimethyl hex,tne-2
Both aldehydes were obtained in the form of colorless oils with a hay--
like smell, which turned into yellow on a longer standing time. Aldehydes
are insoluble In water, but are readily soluble In the usual organic
solvents. Fig. 2 shows the infrared spectra of the two aldehydes Data
obtained from the interpretation of spectra are given, Both aldehydpB
readily form semicarbazones and 2,4-dinitrophenyl hydrazones, which are
well crystallizable. On the condensation of the mentioned aldehydes with
Card 214
Reactions of Chlorine-containing TelomerB of S/079'60/030/05/11j274
Diene Hydrocarbons III, Production of B005~B002
Aldehydes and Ketones From the Products of the
Addition or Tertiary Butyl Chloride to Divinyl
and Chloroprene
acetone in the presence of sodium alcoholate, diene ketones were obtftin-
ed in the form of pale-yellow oils with a pleasant smell The infrared
spectra of the two ketones (2,2-dimethyl nonadiene-4,6-one(8), and
4-chloro-2,2-dimethyl nonadiene-4,6-one(B))respectively, are likewise
shown in Fig. 2. On the hydrogenation of aldehyde (I) in the presence of
colloidal palladium, the main resulting product is 5,5-dimethyl hexanal,
which, however, contains an admixture of the corresponding alcohol Hence,
hydrogenation does not proceed selectively under these conditions
Invostigatione revealed that the telomerization reaction can be applied
to the production of a number of unsaturated aldehydes and ketones with
a quaternary carbon atom from diene compounds All the operatiors Dire
described in great detail in the experimental part of the paper Yield,
boilin6 point, refractive index, density, and characteristic rrequer~cies
of the infrared spectrum are specified for each of the products obtained.
,jtra were taken by means of a spectrophqtometer of type
The infrared sle
VKC-14 (IKS-14 and an apparatus of type M-2 (IKS-2)1%as used in one
Card 3/4
Reactions of Chlorine-crntal~.',ng Telomers of S/079/60/030/05/1 1,'074
Diene Hydrocarbons. III. Production of B005/BO02
Aldehydes and Ketones From the Products of the
Addition of Tertiary Butyl Chloride to Divinyl
and Chloroprene
case There are 2 figures and 4 Soviet references
ASSOCIATIONz Leningradskiy tekhnologicheskiy inBtitut imeni Lensoveta
(Leningrad institute of Technology Imeni Lensovet)
SUBMITTED% May 25, 1959
Card 4/4
65389
,50-
Xx
r
BOO I /BG
AUTHORS; Petrov, A A ard Porfir Y-va, Yu I
TITLE; Invpstipvati,--~nq ~n the Field of Conjugated Systems -X,X
Llr.do of Flectrophi 11c Addition in Unsymmetrical Dleres The
Effect of Benzene-sulfone-dibromoamide or A120olic
Solutions rf Divinyl-aretylene and It8 Romologs
1 '0, N(
PERIODICALt Z hu r na I - t s hc htq k h i,-,. 1 160, Vol , pp
TEXT: Basing on Refs -4. the authors studied the reacticn of tYree
hydrccarbons of the series C nH2n-6 (hexadien-I 5-yne-5. 2-methyl-hexadien-
:~-yne 5-methyl-heptadien-2.~-yne-4) with benzen-i-sulfone-dibromoamide
Of polarization ir.
.r. methanc. in order to determine how the d.,reztior.
,-insymmt*r1-:a1 diene molec-a:eq affects the order of addition of electro-
reagentB The Y~romine atom fixed the point of initial
atta,-k. i p . the point of hghest electron d,:~nsity ht *he -nf~me,~* f
rc-a-icn ~'Refs 5 ~'). Since the aut~.ors found (Ref -I) 'hat ir, vinyl-
ac e I y 1 ~io hyd roc. ~irbons hypohromi tes are predominartly added tD the
Carl /,5
8c~ 389
m7,,. r
i t r -r, rr-
r 7- 1
r r 1 z e 7,-
L or S k
e r, n ~ii
rv e7,a
3-19temg -XX
- - - - - - - - - - -
,,Is r
e f T e s r --i t i r L4 z~ t t e r
e T r an 4 n./ r
r e s r~ r~
e s er. C
r a
,,a t a! o 1, r e 3 7.e -h rL 06
r a i t e r r. e n r 9 e
I
C,
A V
Ill ies t I t I l) q Jl j W,~ 9 7.
A I 1 1 * l (, )f k y V. J.
S , 11 in e
PERIODICAL. Zhurrial obqnr:~.e. kni mi 1 0
TFXT The a-,, thors ----):-,tinuel tne r i ,gFiti )n if '~~e r e a, - t -n
a I ky) .9 vi i t h c -,mpou nd s ha v i ng -~ J ~ b 1 e in J i t r i ~ I e )r-, I a n J t 1 ed
nto account the papers of Refs 4 the ad i , t1 on t I ii m e
~yl, isopropyl, butyl. and terti4rj 5,jtyl to t r me t hy i v t.y ,--L ty e r.
s 1 1 an e - Ry t rea t i np, the re i(_ t i or, ro Ju c t w i t?~ water tnej t i r. e J t .1i e
add i t on prc-, luc t s of t ~:e e x,, ec te J mr, .) ~,i i ticn 31
t ad I I * I ,r. Y 3 3 t :-i t , r- -3,9
s i b I e Ir. h e r, f ra re 1 3 ~, e,-, t r a )f a] t s . f req-1 enc 99
.ng vinrati~ns of a tri~:e an! q:,ene Dini 9.i3tem were f And . t
3pectral reeion wni-h 13 9 t r e ,h ng v ,r t s
of the double
Card 1/ 5
1 riv es t i ga t i on 9 1 n t he F i e 11 o r. wit t e
Systems 7 X ~ I A J I i t i r) n .) f i t i - i m .4 1 k Y P
tD Trialkylvinyl Acetyl e n y I 1 6
,]ata :;hOA that the adju:ts ire m x t ; r - s f i - e t Y 0.'. e ;I rvi it
,ini tha t f-)rmLA I as IV/: 4n i " V ire ritiwll r; r.y A ru w e na t r, e
gi I icon hyd r-),-qrbons ubta ine i fr-'rl. t t' e :i I i Ic t W t ~ I I t t. ; , m A
t~~ , um bu t y : ',-y mpar, 9 o f PI -a r c t , :~ e xy ~tri triret~jA t y q
were )t t a , ne I I nw 11I -~,e r t ~ r e i, it 3 r, f i m e I r. .; ; - i~
their infrared spectra wit ,, tr.,):39 if a i t: ~ 4a T. *. . - am p 9 j n
rarl,ons (DiaKrhm 2 ~ , T~ius ;i, , f rm-i I A ex -e- ! : 1 1 M;i j x
e e r;i t i e t A f- e r, t n e -, e t e t an t' .I 'i r whb r. r
~-'e i r ty J r y -; is. -he nylrr' 'y I a v;-t;, e w i J r
t
t 1, R i H e r. e X'i M e t 1 9 x ar e r, -i re
a e t y ene ~i' I e r, e ~j I -A r r r, t
?
n - e ~, yd r,-. 1 y 9 k p a e it ler.p e,, o 'n r
Wa F, I :T~ ; , - -3 , t' 1 e I T: t ~9 C; ty 1 Q e r 1. .3 e t e
was letermin4l q r; J f e
Card 2/1,
Invu I- i !, Iit it t, , n ~i in t he F i v II , - i--t ' - I I I I I I I , i j~
Sy s t (a tr, 3 XX I . A J i i t ,-n ) f1. r,
c Tr 1 al ky 1 v i ny '. Ace t., e - e
a r r 9 f r ii :t e r e
t i _L.-. Df tno~ a J J -i,. t ir. ixt !-,g.i
h t it i j m a I k 1 9
y I t t I IM " t I; V r.j e
a r,e T. r, s 'I" I 't r.
ir. i x t -i r e f acety'ene an I
tl~e -4, 1 r,y a I ky I ac e ty I ere s i r,19 e i r ve rt l 'T.
the ~,yd r-)wenat . ~) r, r -,.t t. e ., *' the ir. x t.'~ res -i A I t6 :
ma rk a b I e . The au t ~, or 9 men ti o D 7 e t v : Sa' k e
Y e k7c ro v . They ~ x ;. r e:3 9 t ~e ir t t e t k (I e
i rif r i r,? 1 9 r r t h e re o to t e si e
i e t an I I
Tj N ei r r ~i 5 4 f. E!
e r. i ~r t
'~400
A" T P CFi S i- e t r A
ir -ir c- e, y
T 1T LE I r~ v e 3 r. .9 i F I f
a nd Am i z)
P ER I G D IA L -" ?.t~ r tia I r, c- y k t, i at i.') N
TEXT -A ng p r r 3 -1 r; e r c- -f r 1 es
i r, r i rg 'no r o9 a e
Jrate rm ined t.,:t e I i I e rr. m .3 r. tsf 1 r~i e r; it K t- t - r -9 9 r.
cfI i f f a r er t g tru c t,.i r 9 s f J. r e T r. e e mo me ri t ~.p
I/' v; a s f c,, r, J t--, be mu,: n A a r t he r, m.3 . t ~, me! ny r.
R Pf , " ar,~ me 9 1 t y 1 -- xI le Re f Tne i i I- f I e m, mer e
'n m 93 n 1 13 f t t- e - a r b c ny ', hr r t t. e il r. , e 3 tem, q
h a r was o we r t ~i an ir r e e :r. 4 t r K e e e 5 Me T
y9 t (i a e r t :e ar z c i i t t e 3 t~ K C r. e
a r
r: -. e ~ 1. 1 1 r, .9 i n t. - -I: (- . ! c f " , . ! .1 ! - I ~j - I , I - - - - I I - -. I , If f.
y 'I tq M ,, X I I , D , I e Y. ., a. fl r. t zi ~r, lie
f 'I ny A, e tv len#i Vot r.- 1! 1'. f.e -1
O-C
a, e tj I q r. e -i m ~ r, t- e e 3
.3 t v e e r. *, ~~ -~ e i 9 - rn r. a M ~ir,j e M r~ 16 e
-ii- ;ir we e M I. e r a s 3;,,. rate ar. nsa' t e 17 h
r 19 V J? SIM .7. 7n e .9 ~ e
9 ~X r r i
9T t x e r T ti r.
-3 t 13 7. rl IT. r.
r i mar e r- .
r. 'Ar 49 1;,,i wr, i
r. V r
t ga t
e :7, 3 ~ - l X I I - :, : ~ , ~ e Y .- e c~
V j 1 , - e t y i e -t-, K f, t. . o!~ I
A S S A T I t,- ri , n Orr a J 5 k i y - 9 K
Leningr~tj Tecnr: .7. e r e.,.
S',,' ?M I TTE D Y
1 9 rj
TLE.
It ea c t I r A e i.
M ethj I Ain i r, e
PER IODI 'AL D,u r na I s ey i: m i
T E X T ~, Tay. i r, v into af-. :(.,int the -,a:,Prq f 9 r i me
f the r ew: t , of ga tu r ~ t f, d a x i I e L) 7. r~ e 9 n j mr, o n e
, o ri s " -_i
reartel the two acptylene u x i d a 9 2 e~ x/ ~.,3 x -. #~ I t~ ! , :( j
t i rie - I I vi it h me thy I -im i r,,e x p I re~~c tp I w i t t r~
a! - ohc, 1 y e
a mixture ~,f amino
'-
iehydratel w i r, t a 3 s i ir. X 1 1 e
e i: ".Y 1 rr 0 e
ij
0
I nv e9 I i s~h ' i -) n s i ri t rF i e in r
D rear, i~: i x 1 d e a e
?r ,mary ary Acetyer- x i i e s
%,,,- *. -. ." I A m : "le
R*3hC t Cr, x p T. V, t
T mik 1r j,i o r
(3 x e
T' 3 K I
r r .3
a r a e r i at
u r- ic a I r ti -1 W i t hS t t, t li r r,vi r 7 r
I ve!i arl ft.., om j; ou :, I ie ri ru r e ~i r i J,, :~
r o n r-, -3 ha r a,t0 3 f T ie
er-ave i e r i marj 0-- n x ~3
e r,, - y e 11 1 ,1 ~l T; ti
ni ri grAi ski y t eK i n e sk J, -1.
S': I A T I !I
_~r , I r,.,D i In.: t
Lan i r.,
S- -' Y I TTED
Ir
e t r 3 v
7'T L 31, d e f
E R I
TEXT The ai i t ~r w e r er li
1 3 a r. a t ~: a t f r - s en -
ty lene s an I rre sp i r, --3 e r, e , e i J c- e -.r e!,
3,-) t t 1 .3 i r o P e ny ky J n-, 3 r -3:,j r e :3
ad i 'I o r I r, V, I , v 1 z r. ~q T, t e e x i e e r)r- r,yd r
T h i s an a I o I ~; T,,- ~ J t i I j r, m. e e x a e r,,-. 9
~he t p r ir; e 4 ate rT,' a mer - r U.: X
ir '-I C e r -- V ~i re C t 3 S U r, W t t t
p r- s t .9 t eiw u r
ter or s 'C,~ r
i r m i -3 ,1 i i sr,
wr
A I J t f W t
Ac y 10 r. e r--i
K'
1r 1.3 71~ I I
e n e ri th e -,-resence et 't
d r t e
, rt,,: no I ti e t.,- r 1 r
d C0,
a c orl i r. tt h e n .9 t ~i n t 1 f ~i r e 3 i It r 1r. ;i r~ .v. 9 t 1 7~;I
f t h e 2 4 11nit r,j iT.e r, _1:r, r t n e -h is t a e r,' i
k et r r. e E, amp , e kr~owr, -mp-ls t )n 1, A a r C- m
h 1 L I - al j I t I on 0 " a r, -1 r e r. e I t e 9 r f r m
t 1, ;j tcf water -i n J e r ii e ri II 'I1 9 1 r
Ku n e r
t he - r e v , Du s a s s ump t 1n re 07a r I ~ i e s .3 e
a US 8 9 f arl rn 1:~ e T -e e fe -
jy r e.
~a r
AL'BITSKATA, V.M.; STALtIMAN, Yo.M.; PMOV, A.A.
Crioml a try of ore~kn ic oxi loa. Part IV: Orier of addition of alco-v --
to 7,iloroprene oxile in tie presence of alconolates and ~,oron
f I zor I io ot,inr,t to. Zvi r . ob.k-him. 30 no .8: 2')24-~ ~27 Ag ,6o.
(!'IRA P~S)
1. LeTilnj-xa,isiy te~-linologif,heskl) institut icqenl Lensoveta.
~Alco~iols ) ( Bki tui i one )
c A -
K hme
...
C, .13D T, ;I t 11t
r r
n V 3
r. a MC-
e f f e c t7 f tt: 7-- ;7-
f s e -,r t~.07P s
t, f t r. h~ d r,: r~ r. c, v v t-
r, ~i r 11 ,
aF 9 t r q !i r.
A I Hy~r,-cartcn~
A3S C C AT 3'; 7
r. n r
,A!', -U nI 3-
r,a N' . an i i A A
R - a r tn sf I , r . n e a nj- T- r5
Hy I r - c a r Lr,.-, sIV, Rea-t )nsfit', 7-
Hexene-2'~and -D -?~ I, r rl - i i m P t h y :He x,:~ n e2 N
3 o d i u m k~: e 1. ; a eA c : dar, iSA-.-.im Ma'_Dn. A:,,l Ei',~r5
P ER'll C D 1 C AL 'h -"rjg z
T
TEXT . F D rt e -._irs e f 3 e a J S 7 f r
tives on dte~.e s r t:an- sy rL 9 z3 a
the reactions of r- i:.-,.o'r. '
y. ~,-x-ne anq i: ,.I r
mftthyl hexene, - 2wi~ r,s *i U.1143J ~ :T n ar.. t ! -3
F(-,IlDwinj Ref. 2 the sf~rw jni~r - rd . nt r yr, -, r. sr.
saturated ketones wi th quaternary -ar---n at)ms at e r~I t. v-
are obtained fr-) b-,th -~~! ri,_,~g and s-dium st_--t~,a s a -z r i
ing to the Scheme
Card
R~ a- t , r. s D ff C ~ ' -1 r '. n e :-. f~ -. r , -:- - :- 3 1 S I/ - - . /9 - '/ - z - I/ - - ' - - ' . -
Diene Hydrocaru~;ns : V R s~ ~i '~ -. - r. s -, f BCC'/5066
I -Chloro - c. , 15 - dmethy I H ex-r.- 2 and 5-D.:h-. -.r,~ -I I -J~ ::-,~hy
With Sodium Acetcacetl- A--.J and 3 1, --P. L.:i 1 or. i c A . i
(C If CC H CX~-CHCH,C' -X - C HC H ~--il 'H
2 z
(I/ x !;. ~11/~ x C' T!~ 3 K n - s A r,, zi
wa te r f i.' easan r) ic r I f rm i ng ry s
h~-draz i ne de r,, vat ves 7 w r 3 *. n i n 7- wl r o-I 3:
ket-)nes indicate the s f a 'b" n a'~" 3:
the ket-,ne 11~ t~:Pre B n- 1,, y ts 3 '-n
'H ~Cfl - t r -Lns The f r'--i 7.
n I Tl~ss~l.t-
.9 a -n - ;q a r
qi~nd,.ni., a 1 k t- n./ 1 in ~-t: n i v Af
S~Keme 2 Li k e i r, ~-i w 4;
w -, t h 9 A I'J M M n 03'"r th j':
t I
e ', n f ra r Pl 9 .9 rs r. i
a- ; ds ' I V ) an rl 7
rmal...
v rlj' I I9-r F; T I
t he a - I ~l ( I v j .9), -Ii q'i f f I -- ~ ! "~ ' .- " s - T ~l r.
Clf=CH - Their 8em ; -ar~,:tz r. s w r- s -i i. ' h s r y s i, - 7,-.
Card 2/5
Reac t i ~nq of
HY'irl)-'ur~, .ns 17 T~ - n s
r -. - c , c
t~- Sc I I urn A c L t ~a - e t ' 7 A i - d
e r ~. vat , ves ~,f tLe resul t Fir,
f thp resul tant a(71"19, T!-"' e are
'M-rs
f
r
3 j I oj r, A
, 'Ln I e -. r 't 77~ ;is a v
f I , "J r". S r. J '. 3"'~ e
ASS CC :AT Lo n . n K ra d s k~ 1 y t e Y. r, e S k s t m ;j
n ', n 6 r a d T e n r. a I I n s t i t
S - B".1 T ED
Card 3/1
A UTE ORS: Ba I ',y an , K1, - I
A A
Kormer, 7 T-11nd Yak '~ V, r-va
"nsattrated C
TITLE. HydroE4-natio,-, f ~
Colloidal F~illadiuvi. XIV S-,me
Hydroc;enation of B,, subs ti t~Ated
Zhurnal obsh(-hey khimi. , I i(C.
PERICI)ICAL:
pp,
Borov'.i-va A
mir)unds ,n tho 'Fr,~sor, f
Pe-ularlties --f
Al'eneilydr.-)r~art ns
V'-
T a-. T :There are only few dat~i ava~ lable in ;ubi , cat i-,ns
Ppec ial cases of th, hydragenat i nn -~f seven b,. subs. i tute iores
' , T ab 1 t, )In the present paper , the au th.) rg stidy s~,me rul es e-,ern
the hydrogenati,:,n of the fol bi substi t~,ited a! lane ~.ydr--arb-.ns
octadiene-3,4; nonacitene-3,4; de~adiene-3,4; 7-methy, octadiene-2,11,
7-methyl octadiene-3,4; 6.6-dimethyl hertaliene-2,3; and ','-dimethy:
octadiene-3,4. it was found that the first hydrogen mole is usually
added at an increasing rate, after which hydrogenation slows down c:n-
siderably ~,Diagram 1; In hydrocarbons -)f laostri;,t--ire this rule
Card 1/3
Hy-i roEeri a' 1,~)n ,f ~,ns a t,~ r~i C, nJs . r. t,,,- S 7 C.
Y resence of C,-,~l I o1 da I Pa: I a~l ium X! V Some B C C 1 'B
Fecul iari t 1 es of the !lydr-)g7enat on ,f Bi substi t uted
A] I ene Hydrocarb(ins
manife3ts itself a t i I a t i r, - t 1 y TY.,~ ~~yl r ~~ena t -n en c-,q
takes ;,lace solec t i v" 1 j i Nh~-n I qr,, . ng -i h al f D f the a~' a
h
ydri)een quan t i ty a m; x t ~, r t e f ri 3 w, ~?. a d c,~.i h I P t r n J , n a
2- o r 4 - i a u r-z,- d A~ -r. hydr 7 b -,n r,~- a, t a t e:
me
:ase Al k e ny 1 a I I n e 9 e r. e
,>ctatriene-1 natr -.era 4 are h~dr,-,genat~-d ir *n"
same way. After tak,,ne u~ ab-it ,' T. lea .-.f hyiroger. , the read: t, r. r,*.-
iecreases Papidly A,:eno--s ani )~ydr-arh--,ns having a Ji-)ubl- t-nd -.n
end position d4sa~-~ear c--m:'.ete:y -r tr a ---ns,.derable extent aft,~~r
taking ui~ the f.,rs,. hydr,,ger, mr,le Ti.e infrared 9~v--tra (-f !.he !~yJlr-
genation products of allenes with 'Y1. of the hydroKen quant-.ty ara r,-*
ind.,cat~ve of allene -om;.,~.jnds (Dagram "i Diagram I doen n,.t sh w
characteristic differen-es -,f th- hydr,)6-~npiti-)n rat--g ) f 2 , ", fln,i
3 , 6 - d i en e a - D i aeram 3 sh,, w a r u rv,, ~l f - r t h - h y I ro go. n a t, , :r. rates of
alkenyl allenes; D'~at:ram I .9~-,ws tY.e Infrared s~e-ra -;f thp hyir,w,~,r,a
t , on products o f a' k - n y 1 2 '. -nes .1 - - a r n r,- ge n r 't
Card 215
Hydroeenation --, f ~;n a a t;1 r~L * e d Ccm :,"'A nds " neS/--, " - I/ -, z , / : - -- / : - -, , - , --
presence of Colloidal Pa' 1-adium X Tj C,
I X
Peculiarities of the 11ydrcgorat,,r)n rf Bisubs'. . ~ -it ed
Allene Hydrocarbons
The investigation results t~,us ind'.cate t~.at the hydro6enal ' ri ~f b~-
siAstituted allenes takes place selectively, and is alm'.1ar ~(, tho
hydrogenation of acetylenes having the acetylone (;roij, r. f~ho '~nd ~ B~
tiur- In th,~., case of alkenyl allenes,ithe Jirp--tion ~f hyd-okena':-r.
depends to a -ertain extent on the hyAr-.-arbon aTe
4 figures, 2 tables, and -4 S~viet referen,~es.
ASSOCIATICN. Lenin6radskiy tekhno1ct:'.-hesk.,y inst:tut :m L e
L en, ng rad T e cnn o 1 oeaI n a t, tu t e I m en,. -Le n-s---:,v-
SUBMITTED. Oc t,) b,~ r
Card 3/3
C. Ou
A U. 7". ci~ S t31. v v
T IT LE - ke;ic q f Ch i r' n-1 - Cr. t ft .7,. 7, -e .-merD-e i ro-
ca rbors V Syr. thes is , f S A, s '~e ~: iu. -
terl ene Ser. e!' ..,A TYe .r Ar -9
PERIODICAL: Zhurnal obshchey ehim.,., V '0, N_
pp. 3598-3604
TEM In the present papeT, terpene~ ti-F, a i , ee:ie, and p_.:~~#_.rTene
chl-,r,.des were applied to the syrthe:i:s of ner idol, farnesol, and their
anA'oes and homologs acc-)rdintl lu the --; ~rlt, method ty L. MickiA. The
study kitll',zed the terene -,hl -.Acs ',e.')mer1zat:on -f Prenyl
chloride w4th looprene 'j:er~try, ~:Y,1crAe ind ~iperylene hydr',C~.: ;7-.rle
with isoprene :,nd cY-I~r-;rene "JI-r. 1". Gerany. ncetone reSiilte! frOm
-eranyl chloride, and f., :1, ! rmer, dehy,ironerolidGl, rerolidol, and
rarnesol were obtained. De~.ydronerol idol f.ad to be freed from Ketone im-
purities. This fnct,wYich L~ cor.C,.rmed r :y by spectroscopic investigation,
indicates that the purlty ~f many sesq-,.*erpene n1cohols Jescrihe,! in
Card 1/1
~650()
r 1, ri c r: t ;, 1 r, i r, t, T (j,
Dierip Hy,i Syr, thes is ,f Some BOC %'POk
AA'cc~,ols - f the Sesqui *e rpene l'erieq -.,rd T, e '. r r.;, I -)J~ s
pub 1 ic at i )ns is I '[~~U f f i (7 1 e(A W it ill) LA t i rif- ti,e i r in i-v n
,-na I ot~ous mai.ne r, the i m)v r!i ,f I Ojy (I rto,o r,) I i do ) in,] tit- r,, I I do I we rp ob-
t,i I no (I Fr,jw I -ch I o r,-,- ' , - d I me thy I -:,c tit d iene- '',F,. i.e., I-
dodecad ien-f, , I O-in- I -o1- and 7 , 1~- trime thy 0-
The annlogs of the at cire-men' ~ ~)ned ~, r du c * 9 w it I. one chl,)ri re itorr, instead
of the me thyl e-roup , 7-ch, orc- 'I ',-di me thy I - dodecadien-, , 10- in- and
-o ()r(
chl,)ro-1,~-dimethyl-d(,fiectttrion-l,t 10-o1-1, rosulted fr m 1''
-7 methyl-nct;tdleno-`,~ . Tho:iv all c-hol:i itre col -Iesfi, l 113' 11 i", !!3 wi th
lenniint A(ir, ind difitillxiMe -. 1 1. ut c-- n r. ' ~.e inf-lred
s,, e c, ' r a ., f tLp --oea~ 0 c m t-ii, .1 1 a s s i i-r.,, b : e f e *~ r i e
- I
d i n t he end ~ o s i t : rjr~ , fir. 14 ~ir. n ', er, s e iG cm ta r,d * ~l * 1'. e s t re I c ~. i ng
vibrit-.ons of the CH -rup. The valence fre uencies uf tf.e Aouble b,),nd In
tl~e lectra u~ llco~,.olls w i t ~; ) -,. ' cKlcrir.e ." .9L,,w a weak Int-r.'31ty. T~.;'
!.e j,-rou, ir. 'A.t, -CF='A-.,- ~r.
~:-f- plency. In C K n e rv) 1 1 c rr, r,., i n t e n,3 o
d 1 C t i v e f v;ri~ I
Us ,
C