SCIENTIFIC ABSTRACT PETROV, A.A. - PETROV, A.A.

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CIA-RDP86-00513R001240410012-6
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S
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100
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July 19, 2001
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12
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December 31, 1967
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SCIENTIFIC ABSTRACT
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nV :~s t 1 g, at i u ris 1 ri t ?~ .- r .- , -. , I t Cj n t h i n)b i em of t n 0l :!3oprt-ne o, i t h I t s e A-E I A T I u N Le r. i r;..- :-i po, r -i T e n L u -'I T . ti n r 0. -A v I F ul~ 3 %U' t 'I L t + t 1 a e v1 a Li:.,gi1. S-. "f t 1-.6 ,!tr tr, -i Ir.1 - ! t' 11 . " : I jw f- q ~j r ': I 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 , , . a di ti on r r ( I t:,.- , i :- ~ t j !,,-) ~ i ; - m , - ., ., * I , 1~ , q - t - I 0 rr 'a I t I Rr t f rfl i t r. q i r- T n, rp r v t oi lb r o m from ti,t. s - t k, Gr o ~n i u, c-.9 11 t h, s r, fra r e o -i t ti r: L n Cc 141' 1 t fl -3 b r- wfi ap r a ne k1. t t I U 0!.3 e r es t I ~l at I L, I's lr~ t h r r .9 t I f., C 1 1* I (I() " 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, I .. 1, ;1 r:t , ~ '! r I' " !:A t It n I A, K a I k k!, ra r 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 ! f Lt. - , al, I 'i r" ASSOCIAT.Cli: Leiiins~radsk j s i s, tul L-~r,8 v-ta " Le n I n~-,rad r r. t. i T, s v m,~ r Lt n,,3 v SUBMITTED. ru, Card 3/3 ~ (3) AMIOn A 1 ' b i t 7. Pe trD7; 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 UL TT E, .7u.,e !9, Card 7 )/3 5 3) i, U-j F OJ,: IT LI: rov -e1! 'j, Con U., o f the i t t r~, 1z o e;, ~t- ' erle~, V. 1"', C I ;' - iiV i 1, e - Ep I o L - T R X CT iriiti V' 'J 0:.t ,LL[)er e i1,' " i 11- 1 1, It' 1-~Ct. (I i th ett.,Yl-, ~,rr'pj irle" ';;' e of :%er,7,j ill ti-.e 1- e'- '7olncric ke. 4" three I - I , r v e ab rup t 1Y j on--A-,-ntf~ .he c .,*: iel . e exi ut 0 e d Caxd 1/7 W Thus, x e 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? Card 21-~ ~md 16 refer-_-~ices. -)f ii.i7:. re 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 * " Ul !.' TT'" --") : " un 0 , 9 , 1 " -3 I - Card -~/7 N t r M t i Tlml 1. -E,-4 i r s o v 7 e a, t ..j i u r r ia I a 1. im i i V D 'Ir ;,T. .'o!:e u I i c ata cyis -L-re av ai i L D e -a 1. 1%, f; j,. tj )n 3 re,ictions )f diacety:ene v.-ith u I'd. ut ).,,Iy irief drLt;~ ~.re re,~,,O-t t) L:. 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 ,-iriin es via-, c m. r~: e r! t '.P- i r i~. e fre ae:,ci e "3 f c y ,-I e t~, I -,e: em fe rapid I.- t u r,, 1) r ow;, krid i :ii - d c e e i.,;,9 n I v-(i C Card 1 Letter to the A i tor. ,l,' 1 ti ).,, of e!jc, //I!_ p -.- - molecule at the triple )r,--,in- ! , , r-,+~ , . e 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 SUBMITTED. I.'arch ?8, 1)"r) Card 2/2 A A YaK - Hil- r t it tr - A L 3 S.~ r t ang 4try s 5 n ffff, lip .K Y 9 t 'f~ FJ rs t r,di rl F.,; t K t r t f ~tipry: t, -frai, S Tr ~r s r - t h pz r an! T e e n g t t r. - A r -i i s Ej I f e a r s t a r e to f t 18 Fr y f t I "7a-- t a.. r e s j w r. 15 t 's q s s -K r, that n n t ra 9 b an a c ral - :-. . -C t.,t~n~ 9 1 13 t d -1 9 s Kn a r. t r-r, -t a x .9 t ov - r. t:. a r 1 2 ifie ~,-ii3 in thij Fitt, I A' Syntema - 5 T ,msi r I z at ion L, r r e -,r.: )r,-~rene n i e~r r t -me r s The roduc t obtal ned by F.I. ~ar~SK ar,a 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. .,T~~,und ,9 admlxo~vi t,. t~..,q ?e s es a : a r r. J. a t 1 y a k t c n i? a a a t of a hydrolyt e r n a f r t:-, e d,) u b n d " Ih e a r 'S' f r r -, wt, - ~. q r e i e t - ASS-- :A'~ L er. r a J.4 t e k r, g . 1. r. *- 3 y " n s t t a ir,,- ra I )gy !i Tj X:, r r % to r ~,i a c ~l c r Ir.c,ef,iS,:s tf,, -,j r. t T:, r- r~ v r r. v t- s s, C 2 S .S 2, 1 9 r 5 1 10 T 'Ir AS S Jc, -A,' 1 L y Card 2 '2 'A L ~ Continued !'. I " - , A rf r'] t r v E7 t 5z v 1 T7- a s 33 AiTiluit'- j 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 L,~ ~- r t(; th, z-di t z~ r . ~,, .,t iij. ~:~ ~ t 1 _n , t,~t,d Li d,, fre,jen-,, Jr. t 0 t ~.a t r-a 1 t, a I- r, ~~ I ra -f' ar, feft C r,Cf k Ir 1 I C td t Tr, in I, e C :AT I Lei.i aT _.a Mla YZ5 5 9 rc 2 5( 5) .AUTHO-Ri: I e , r c.. v-,- A r T IT U; (,n t-.e qr" '~i*~...' bUty I W~. I 1,JY tI KJ 1 tf c Ml 6 r i 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 . : ap I ar r. t I c u rs ic r d i t 1. e .9 H: - e r i- ad - a c s w; o !-i t; r t- L, ov,_ v e r , ai ar e j I~ Card 1/5 c,, r - j , a ! . r t ! e r 1, -f ~ .- ::_~ r -, a ~ f. ' I In *.re m, t L r-l :r, L t Butyl 7inyl -a~4y. A y zi tr,e att r i :3 ~,e r s t rosi,-,ue t h e !ij d r t i Yakuv ,evuli, Tnoi j. r v e f r t 1, cr al I c u 3 v aj 1 t h I U:T, dt,ln n t~.e tr 1 lithi ,im - , r ~* i ,, i : )tiq uridt~ w i t *,, - b, rid a r t~ : : - 11 1, : el i n t he f c " m j (j ~,-A j h ~ 1, " " " r : , ~ - ! t~~e ~OlymerB. ii f- w .,,/ s? r , :. -: d e t v c: t -, d L :-, ', h f -Ire J s r ti ruL. Card 21',' T 1, e f r,~ i . e .. !- - -- 11 , : " :. 1 On thic ombinatllon -f Buty I tu Vi ny I -a I ky I Ace ty lene ii apiarp-r.tlj ir, t.,..- r,- -i ing 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 g o uy u f k I I e n hj I r - c r', r, s m , t n a -~ (~ s t ~- s i " d p, s 3L t i c, r, ~ f t me A 1 e:-, r i , i n K, m d t e c a,- c a I n . T ~,e r o a i e ! ' . i- , t . v wlilclli 'I:-P 5,V1, t ASSG~:IATIONj L e N 1 !,f' ' - -' J ejt e SK I I t t U t 1 . L~n i %,; r a r, !jti t t - f c ~- t. zj -me r~ ! L e- a 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