SCIENTIFIC ABSTRACT KURSANOV, D. N. - KURSANOV, D. N.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R000927810003-1
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: March 13, 2001
• Sequence Number: 3
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

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3926 The Ittlect Of Structural Factors, on Conivi(all,m
Phenomena. 1. The 119blilly of Hydrogen Alom. lit
Cyclic Ketoness of VaAmss Structure, A. N. Nesmr.
yanov, D. V~KuFjanov, K. A. Pecturraltaya. and Z. N.
Parties.
Iffavy water *401 U*Vd for the xUbaMulkM 44 t) for It i. the
4 Pt)hjikx" In Cyclic holonem. such RUIPAMUMM" are c4irrelAteti
w1th the Ktrwral mobility of the If attim in %h, *vqwncr
C11 CO that muxt be regarded an I SYMOM -4 CoAlU41tated
bonds H -C C~0, analogous to the kwwn C-C-C-0. 7hust,
in cyclohoursonst all four a hydrogeno, and In 2:2.6-tri.
methylcyclobsixanotur the unique a hydrogsin, are replaced,
whereas in the bicyclic campheoilone the reartion is forbid -
den on account of the presence. in the e position, of the toot
of Our - CH,- bridift. in the procedure adopted the substance
Investigated was heated Ifor 50 to 70 hr and In the pres#rce
Of X.Cq) with Water COAUAIng A knows; quantity of V,0. The
reaction product, segarated from water, was analysed by
charring. and the formed water was tested for D content by
the specific gravity method. In this way the number of If
atoms replaced was determined, and the result ssr;s~ checked
by the 0 drfect in water separated from the reaction product.
asy"LlOWGICAL Lglt~A?Wt CLAMICAIM"
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U&-,:4/Chemiatry - Alcohols, Reactions of Sep 48
With Allyl Pyridine Chloride
Chemiatry - Alkox,7 Groups
"The interaction of Allyl Pyridine Chloride and
Alcohol," D. 14. Kursanov, 0. W1. Shemye-kina, Inst
Org Chem, Acad Sci USSR, Moecorw Textile Inar.,
3 pp
"Dok Ak Nauk SSSR" Vol LXII, No 3
It has been established that an alkox:y-methyl
radical changes places easily with hydrogen in
the bydroxy group, resulting in tranerforzaatJon
of alcohols. Attmpts to find 'if this reaction
AIM 36/49T14
USSR/Chemistry - Alcohols, Reactions of sep 48
With Allyl Pyridine Chloride
(Contd)
can be extended to quaternary sults of -cmia
vith other radicals. Finds that allyl radical
and alkoxy-methyl radicals of quaternary e=onla
salta behave in the same-Tashion during inter-
action with alcohols. However, In tbia case,
yield was oaly a little aver 10% of the theoret-
ical. Submitted by Aced B. A. Kazenakly,
13 Jul 48.
40b 36/49TI4.

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0 C'.A. 42. 419~.'~ ~ Qu,tt,-rnjry anintimition eaki, t~onig,
- chloride ('101 ;VI') ill (lie alitive give 511"
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mV 1,4-.,N.

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himilAttv, I -id.. Chl'itillrat Pul g..vu linoAc, while PrCO,II .0 1.141 41" l.ivr PtCo.- I
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Sill,ititntion of 1-(tiocyloxynie
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Exchange Anil cleavage reactions of quaternary sunniss.
nittris ulls III Reaction of quaternary ammunium "Its
with asters D. N kill uAIM 1114 V . N. "titkiii- Itreit.
Ah.&J, \,,.k .~ N N P 014ef Aht-m. N,jmk 1949. *.174 zt,
-%I ( ' .1 - 4J. '-WI A I Bul"'I I '.1illu-4111i .... I , Id".
still, ill, 11 1 .-d A I'lls'll" I.. 't 1'. . 41 1;0 ", IlIlsv
If ItItIA, .-,,I it Uist,A, to - , 1, - ..It ". ...
4ulciAll-C I-W,. Omyst,flhy. t(j,odsisoon hb,sd. I I-IIII,
and UNI a FWA, ;t% fit Ist- it W, *-'tl,',' K4v,, Pilf x.
OAc anJ wel"P. b... 118-11, . all; I I;."-
.3 lnl~:8.4 I -I..'Ylpyriffinilit" chlurkle
hris. at JW,
. ive pyti4lulc, 1.5 g. U1011. 411d
US(IC11,111. AT CCAtwn pt'll"bly p(mcc,lis by
fliffluipm lot ill m1111111111 'Irfly. ;11 the 0 sit the r,ter All"
ch-Av~cr it( the k Kt-sp fr-ts the quAt"tiify c(uttlosotimf
M Mechanism of the tosictiona M quaternary amtw.
nium asiltit with alcohols V N 1~iltm% m,11 It N. KuT%
1-111""V A .111 14; %1, 1 !:1; K ' 11"I ~-'l N
x " ,, 1~.' 1- m Piss "1.41 KA- A": dl-lie. I-
Me d" W elk'r 14, 9A Is *. -1-1 t 1 14 C.% III,*
m,I :ii" ;- d0e, vi ',. 041 7% 1:- it
.1! 1 111 1 st t..... I 'i 11 .11V K.sv,- ill 11 fit. at :0
Ill'; If, '14", 1. 1:o .1% f-.-
Ir I Ill,), -1 .1-1.1 .1h," I". 11: N %
,I.. is . 46. 1 1.1 1'.0mil 0 K I O."l-I It,
Ofl,~10, A.t.t 1% .1 14W11,011 1 1.,.
INI ~'W' stave 311',' 1 V` 111141(11,1-ls~
I.IKIll JIIIICIIOP~ the
twill YlityTislillium iml. sillos'll by thepsratir,111. It.- Is'.
The Frstilt,t tire tfiscu%~tl ill tcrnit, ci( f1watatiqui of th,
priklurt% thrmigli oumittin dcrivs forlunt from
CI,.,VAs;C of the quat.m.,ty -!I. C.. Nt. K.

Influrtice of tho structural (actors an co"Jultation ph#,
nornims. 1. Motr'llly of bydiogen stoma In various cyclic
1.9tones. .4, N. N"inryAtiov, 1l, N, -W.,tio,v, k. A,
lWhenk., ya. ind Z. N. I'Arri- - itc.'C&7n, M- -
ct,w). I-vif. Ak4d. Sauk S.S.S.R.. Otild Kism. Nam*
1949, W2 T.-L',2.tl.Ttititcthylcycloheitnotic CMilpictely
1.1thijig., ,nv If bw a 1) Alom after 70 bun. If LOV lit
41111"lud 11,0; vvd,thriatuine tefungro 4 If almst, Itr
I1 '46,1114 ut N) ht, At 101'. ~%-
Imtirrit 1 and 2' It awim fut 1) it% 70 ht-. at 1:10 ',
vxubmigr ukrq plmv with rjuiphriiilogir tw cami,h-'r-
q1till"tiv; thil it vild'siff"I I'T Itout-li'leff"r .I ,,I,jflg 411"n
1. 1.-.1 tile CO mut Vil. "hwh follow. filkil 11101 ,
ttile. 11. Mobility of bydiosen stoma in atetyltic.lons
and Ital Cobalt and slumInUM salts. A, N. Nv,imvaiun,
1). N. Kumnov, 1'. A. Smoliju. and Z. N. Viffln.
16id. 5qA4i(XJ.--CII,Arj kept 70 firs. kkt 11 ' 111 11,0 en-
fiched with IW.O In file larvilre oif flitmVIC Show"I rx-*
Ow"ge,4211 (within 15r;) fur2 1). rheCocat aml tile
At calf -how im enrictinwtit Ity D. The rr~tik I- i
... t tile 1.1,k o1 illil"'it'ility 4A conjuxitioll I-( II-x li,Okl 11
CII lg,ji,l with CO doe I, J~rj 11,11vill.krity "I tht .,%. , .-t
the CII link and th.it 4 ;h" 114o"Clion v1 the CO gr.*$I,.
A% well a, to Favtv,kil'~ vulc (C.A. 35. L'MIPI. %hith
I'WhO, allvile liliti.116ni it% 0-111ritilwir finjtc G %I. K.

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Roacition of quaternary ammanluris %&Its with others
00 11. N,-Kut--&il-lv AIM V. N. 1;rtlim., 044dy .1k,,l /0 00
Xj k X.N.S.R. 63, -M7 -,'Olf PIN). -Fil IC11,111% 1:1 it i; -
sn'l W,5 S. I-befixylpyridinham dil-ni-le At'r fir, ..t
NW JW1, lpvc, A 7 K. %allreact"I rtficir ..Ii,l 1.4 T' I'll.
V11,Y), his 172%,in't thr.,64W -t. A
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W-Ulet AS the ph We. M. 13
. 141,( l ( I.1 " .-A
chlocul, ill', g - In fit.
gave I I -A
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chfori,je, h,,.. W5-1.5 , 0.4%. C,J[;,0i limi 11 01~, fir
1114 4"t 4110 4 194 7.1, it V 1. 431M. I Ild V. "i, i f 'I / ~,
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1
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90 1-91 1*. all.' 1.001, 4 1311411, Phi'Mc -J t 1.-0
IWII-IiIIIIIIII dif-wi-10 ill 8 brs- bit It'll ~~kl K IV- Li W,
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&ML pheivylineth.atic aml [lie 14.10 detiv.. - it,11 I bill,
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11111chandir reaction$ and cleavages to the qualefriary aul.
Moclurn gait Foup. VI. Rit"flact at iialits of alkoijoisthyl-
pyridinitun w th h ols - V.N- Setkina and 1). N. Kur-
I I art
,vuly. Fkdj. N,juk OPPI Xhimi. Seek.
1930, 3.4-iLl; d. CA. 41, 49~M. 44, U170- 1'4#X,4j and
ilsikesir-AvIll-kheris"t falls vichl. it- plisnalty Imcklurl'.
plicayl alkil AWMA,; lCk10tRIAfY le.1clic"Is MI.) dtalkirl
fiWill.41" phrijol lot InAl, lch vile irmins. anti aliptlaric ales.
The diAkyl formah react with ArOH. yielding ROII and
lite mills. (pho'clis 111) '"' to Feact with pyritline-
lbrotonated
I ICI ~11.iilg 1-1-tiOll Lhittilsol.yiCkfing
hi,.h vicAve into PbOll asul Ph()CII# ion.%. the
.0,11104 W resin bY
I.Alter vmlyiuK the chain rractkin that Yields the xy-
,uetT%,ivc ad.111. nf If kill. IIcAling 4:1.2 t. 1-01110
itle: hyl)liy, i(jillillill chlofiar till, inin. it)
Jim 601t.l.v It I if 1. .It IC I t I a k I 6c 11,. 14.617, B It 0 CHION
1". 127 N' 1;' 11 97:'2- N)I. 1 1.111, 7to% reltin. and .111 till
ti Ill., at 04%e V."
plijkline. KH'I 89.7% 1-ill.
I -Orvill-iii Vill, thi, Illy(Whilutil
in I hr. At IM W L At; 1,11011. a% Imyl chltxWv, 4.8 o
deryl air.. :oK~ dr(yi PA htfeeal- bl'-It 18""' $'It" ""
It jidecyl foroud. b, 2118- it)*. 0"
% r"n. I-(Trlr-jrVvl(j%v-
1.411h. and 621
- jjkj,djj,yI p,afal, ni. 12
12"c
1
(9 0 Al"I 10.2 9. 1-(IttF.4-
I -ll1vFtmitfillllllll clillside in Ill hr-, al 111,11tiv) .
fornill. IsIrTwine.110. 'Intl an un.
01.1ed vie .1,1 ,1 r_lll: I.n.phth'Al gave W),/Q of be IL",e
1IQlILJ AIIJ A,, alLdi-I. 1_1,1. III-At ... it 4..*, Pholf ..AI
LN, 9. (IlulAc f.
Ili 3 "' his' At lfAl_1A)' 94vt (W.' IJ-Ull arid
4 AV phely)JI(irmall1rhyde resin; 2-114ijbillul reActal I Mi4lly
licit till' 3'9 S' I'll()' 1 '&it" l() I (OfInAl (I hn. at IN)'
9)* 94%r M 9. ithyl all. 146% ril?
q.1 J.6 K. r"ll" The 4timence
OhClls in lite i. iq tile f,.Ik)ning 1,ct
heating thi. jurinis ~ it) X.) mitt, pyliditic-11cl Ili 61.
at 1.5 x. NA011-1. fti&n. 36-p Pholf. and
4.7 a t-lis.ril .411,f Ol't it. W the I'll, if I.

Cop
"oil of SUD"Wal fac4wa on conjulation pbenonlona.
111 of h d *a atoms In the dlb*nxoylmttb&Ao
to kj
N. urMov , Z. N. I'Arnts, and r. A. Sutnl-
~ta. Inwil. Mad. -Nauk S.S.S.R., Wei Kkim. Nauk 1950.
A12-17; c1. C.A. 44, 31,117d.-Ilrating 13I.Cli, with 1110
enriched with LIP 26 hrs. at 19' g;tve no D-if exchinge.
but in duniane-1Y) an rickingr of I If frmfilv i-k Mme
after 20 ins-if 0% at 17' or 410 -juc.ho .-r I It I, rz-
rbjngnl, and at IrW Aussat 2 If um
gives SirnilAr results. SteArics6l. nlyfloyl ale., and funiAlw
" give only tractional exchange with D.0 ahme, but H1
aildn. of dioutte the exchange is nearly complete. The
fewlts art latcrpreled u being the cium-quenct,-I es-entiAt
fil'WAY. u( I he given ctsulmiumi'l In I 1 4) it"11r. C.- M. K.

mf -Clefiva -go reacti Ions-ol-111T A-r-y'
Af ammonk
, VIT. Refictlon of salts of
'&-Cqji~ju-~j With Ilkyl ethers of phenols. T,-N nov
wid V. N. SA,tk:na. hwevi. elkad, Avik S.S.S.R., Oidcl,
Ehim. Nank 1950.051-8; cf.
I ~dccylm vinet hyl)pyridiniu tit chlari(le with -W8 R. HtONt
8 lit, to ISO 95' (qcalcd t0w) qavc- 29 g. 14011h, t g. (lc,:Yl
C111(idde, -1.11 ig~ 41,:Cyl COC" II!, Hl" 1.4378, (11," OXI-10,
2 g. PhOC11,oC,.11l,, lit, I-loo-V, vV (11,1 0.9-1 to,
and 7 g, ( ClX,,()),C11-, bj~ nit' 1A 120, (11.0 0. N 11 i'-':
-.;-tnr ';-2 g. (Tg%~ %V11; 5VOIrvil
from tile irc!d'hirs.
pyq g. M10111) G hirs. nt 110
11"611, 1.1 1'. (11110'VIC111, 1,7" Iv, g'-'% 1" '1j:' 1. 107,11.
till 0 '~ds, 1. 1 unkii,i%,t TuH,01re, list] 1~', 7.1', atul 7.7
9'( Pit".) reitt.
C . r. 111011 C, to INI ':PW X
( IJ 1-4-~~'O %t 0 ,
deryl at-. and '2'(1 R. "'OpI wv; Ch'ti" M fit'l. Ib, it
11.1nivwd oil eltillpt-1 "t"" . % forill ol 1111i w,[ f- w
aldeby'le lr'ill. It, fl., )':~lidillillw dt, imil-It",
t-;. r lud 11trit t,'IC, the bit'llAitill lit 111,
pnlyllit-de rv~ink. Tli~ i~;-'O;wj 0 j+c1tol; -In'! 1.1
ttlicirr, with r4llf ; n!

XtMSANOV, D.N-,,~ KABACIINIX~ 11.1.0 XAM- ZMA~ Ye.D., PMIMIUSVA~ Ye. N., SOXOLOV~N,D.
and FRIADLINA~ R. Kh.
"The Current State of the Theory of Chemical Structure," Usp. Khim.,
19, No.5, pp 529-544, 1950
Translation W-16104, 30 Dee 50

KUi,6AfN'OV, 1). N.
N. N. t;el'nRov. A. S. Zabrodina, D. N. Kursanov, and A. X. Ruzhentseva
"S. S. Nametkin's Work in the rield of Petroleum Chemistry," Uspkht Dimii, Vol. XIX.
No. 6, 1950, pp. 6U-672

-4 of Me 90WAud idefte Ga =1411,1411 9118-
name". L x0ff11V1( AduW92m to Cyclic ket4ass
at durecivat StMUMM. A . anov- [==-r
K-A, poch
zopilki U0449. Gotv&rd., (144, jW, if. V. L~M~OS,4
No, 132. org. KUM. 7. *441m).--See CA. 44
39kU.
.
It. HOW#
I of hydocau MOM (m "Atytackwo "A COW
and dl A, U. Nestuavauaw D
14; K T
A
ft
i
IQ
------
.
.
ol
tts -&W Z N. Parmft~ -
.
b24---See C.A. 44, 2917f, iV. jZtWty ad "
j: UzLk - ~ - ,
-ifi. 329-306 (from nt 0 g.) with 1.47 t.
k
i
,
ot katactes a' diffloctnt c tkM. A. N. Nesmejuttav, c
dioxin,*-90* in (ClWljo moi Wt Overnight- tbm ctcsted W
oj,,*t filetted sad
K. A, Pceftenkmaya,
! r., Md. W-72; Aq. DaM, Wivi tu upel the Or
,
;a. in RID dad
u'Llram
it it
0
t
W
1
4. CA. 45, 4009
~ p ecan-d-one In 150
- 4- 840 was 4awlY altdcd 1413
X. Pond. hrablHi- After
" -S!
.
w
3a
10
evapd; gave 98~
p
;I ~ 2 64HW41h*1-
w-,jTmphAle, Statuatty was obtain 90%1.
dik#rc;L-.
d as Yj tall
Ute
i
Imthii; to expet all Mls. the gate. was created v6itb 58 C.
"4(et- dikf. With 140. and the am. layer sepd
and washed; _
.
sn
4.1 aW warm PbMe, camphenyto" f2ited tip'
I U'0
.
distn. pve
1
2*
101 in I
mact with djaxane_S(h.H (2 g~) 1. cocti. licl was
wit . macm al MCONO
a a slow It.
lin
i
i
-
. n
j 1. . do 0.98 3. Ilds (a C.) ht atto was
treated tvith 7.44 9. (1101mue-Ur Im EW and after 2-3
tin ce coo
th
trisu-j w
g
over 6 brs.; :I green color developed sloug with felm- Of
u
.
OIL cf,10fle's sclu - was washedwith 10,C0, ond dhtd. ykId.
1 I tj colotless T-ndrozo-H, ra it 1-120 (hota =h-PtEf-
j3
64riuWaYt
j
n of 2
t
1,4 0,P 9. unreaciM aut"W jLzd &1% T-kalme 10fiv, (1).
*
1 o
.
,
ber . Similar rVact
_
35% deco-P. 113-1w.
14
#$
1,5210, do 1,32M. Sindlar remetiou of 7
.
%j,lm%6jdc(-
m-6-tmc with 113
di
9% vve
run at 45-
henylolle f,,IitA to PIct with U,0,No. Ue lick of
m
.
C.
uaxe-Hr 14ve 72
a
decow a
p
polsibuity of
~Jvlty Is a(,cr1lxd to im
rcac
Ps. 04
exim), Ike to *It YkMnt iff1r.
I
~
coulugation hctw.~Q the CO -,WJ the adj=nt C11 link.
Ica-MIAP01
M
G
h

fvarione, h. 178.5-0.60. xV with 0.5 C. diazattem
.
-
,
i;r Sh"INdY Vve 80% "tons clerfv., m. 37-8s. Cam.
_
vJr6iAxi: failed W vemcv_-wkh--d6a=ze,13r Idler- 2 -Us.
YvAhreing in Rtj(). 1 (3,30 c.) sad 0. Etto
"
Vjt'j.j,L,l it Orignard mag"t wh" trou
t-4
gave
(13t
luoltyt,pirodecurone, b, RjF*. x1j 1.48W. Adda. of
11~0; t,. (!~XNJ[g)t to 1.15 Z, 7-hruncapirtifUldtcati-G-one
(allowul by watining lt-d to a viCtirms rcaction which was
accumpunicil by gas Irvolutiou; treatment of the couled
nrr

Exchange imd tleavalle reactions of quatrfnik=MOGittnt
"Its. Vill. Reaction with alcohols and ph of sub
stunted antmonium &all* with a benlyl radical. V. N.
.1i,11,111A a I tit 1) N. Kilt-~.Il I, 1,,~ 111fil. A kit. N4 if Al S. R
Orld. Khm. Xifill 1951, M14o; rf. C.A. 45, 412111p K10h.
4.%I1tVfl.AfY IWIIIYI ratheak (orm
-urtritimpAing &14-%.
with alm or pbruok Im,nivi rtfirr4of flirt
W I't"dUcts of ex(lung'. of tile ultiltile If CA tile 11he"01% for the
I,hC#(l group [Kith fil file, Oil group ill well as in the ortho
mid p4ra po%iliuti%; with nalilithols the reaction Is pfellonn-
mintIr nucirar subititution it# the who anil pam tKnitions
.Ifhr~gwct toolL If-ting 16g. PhCH,.1;?,fe.PhCIand 9
X. AmOll 5 firs. at 140-55" gavell.4 g. PAC1110.4m. hit llf',-
7",d--0fCA1I42 r1lPlAWil. Sitnilarly.13.4p( 1-benzy1pyri-
'11111turn chl(wW; (11 anti Ill K. Co.11.011 8 hr%. at M-S)"
Sol, 1.4--fl.
gave 7 g. I'AC11,0C,01n, 14 .17-24".M."O.M84 j
hydfaity"phlAtilegi. tit. 111-11.h' (From N)% TICOOD.
in,- It ZI&42* (cmdo, and 1.2 g. CallisO .M. ISO.& 90.0",
1, CC.,k,-.o stimlirlv. -"C.h I.C.1i'l III
41.,
. . I in G Ill, 41 N) jc~,t. ulne-l"I
ju~phthi.l,;Ilr~ In
1.5'. J1141 !) .'I K. % i.4,11, mI. conlIKKelof ,,
I ImCittm, from ,hich ill %Ill. with ligtoine IfAir I it
E,:'Lliso, sit. 72", identilwd A,
i,w. 11-tiog ISS r. I'litlif ~,th 41 'X. I ti lirs. tit
FAIC MICH. jsl~ No4'Jj:PA. tit. NW. fit 143-1,
Ser
I
45% ~)Ir~ .0111ot 1.11TV tit, W. And 171,
4,1-1 14 M.

0 0 0 0 0 0 0 0 0 4 0 4 4,
11 11 11 mis of to is I, a 81 a 0
AO
MAGIAR KIMIAI FOLTOIRAT
HUNG,'.RIAX JOMNAL OF CHEMISTRY
VOL57, -1951
No. 2, Feb.
tl.,V. Niogroaftop
Ord
*0 quamloll ut lim pfcarni mate
of ckwwk)al istruclure
Wruw $be fluallwan) .............. 41-461 coo
coo
00
d
see
A 0
of 0
,so
00 # .i., a i a I t a too
04 1 4 1. 14 :10*
of, "A
U
6 0 00 0 4 o's 4 0 0 0000

~77

LE Rxch.;rigs reaC11*0 fiv
tisdltd Ily means 0t the kea ivA*tt

0hamical Abst X, K(IM11,11w, Vr, NKIXn Ir awl f Vfvll-~
.
A
IN` 19
1 =Cri, ca
s
Pr-
5
, 'rtaction
. take plim. lo-r~
Organic Chemistry luakatc with D~-tlrichod It Dvcr t"1 F~Ev, (fie. ('t,'co~.
'Thk w&% heatcd, with pJyficx%trcthj'vw rilwaa! ill the,"
-
to ALox utge IU bri. at 2:01 anA ttt. f k%'A-ll iA4ltC-d

mmf,34%, vuharige took pl2cc audcr th ~ n'mve -(110itions,'
Vith atl 06 0 C160 ilt the Mitt. of I MIlte ll~ultru estcrt-

TI
A
chlin unit
MCHI)OMMUCO-1 of the t,%ytsfrrcJtmn..:
&E, K(mnlqoff. A

~7
U77.

The mechanism Of t a 92 Polon by means of
'J!�~Uterfu if. I/ K, A7.1rov, Z.1ret,k.Avn. Z. N.
~-~P~d U- p.-Nurs-knov. ims 1.1d. Nank S.S.S. R.
ins. AldNAls 1953, 519-23; cf. C.A. 48, %'71c.-
It was previously shown that cyclization of 2-methyl-1,6-
hexadlenl-one fit D-enriched IIJ10, results In the entry
of D Into the cycloprutcnotie deriv., Indicating the cor-
metitr%it of the loult: onttirr ill the reac IIon ai propmed by
Nararov (C.A. 48, 611d). fit neblett In the initial atep D'
tulds to the terminal C of the allyl group. The locatinn cf
the D In the product urai now investigated. The driftcro-
2,4-d inurthyl-2-cyclopen ten- I -one, obtnined as described
above, was olnuilted. )-iddills 110,CCIUMCC11,120,11.
which contained stib%tatill-illy all (lie D fluit was pre.4clit ill
the cyclopentennine, Thus the preience of D on tile I-,
-2-, 3-, or 11-pmIticins Is excludc(l. Oxidation of the cyclo-
pentenone with ScOl gave D-firce 2,41-dimethyl-2-cyclo-
Prittene-LUlane, m. 01-5*. Hence D mu%t br. lit"ent fit
file 6-position, Le, tile Inethylelle group adjacent to OIL
carbonyl. This shows tb;tt the cyciiiation is entri-ed not by
CIIt:CIICl1mCOCMe!CIIj, hut by Its Isomer, MCCII:CII-
COCMe:CH,. No exchange of D occurs between the
.sycl-pTntenigric -dCTJ,~~._;Lnd_ASQ!I-AcOD. G. M. K.

tj
USSR/Chemistry Isotopes; Nov/Dee 53
Hydrocarbons
"Hydrogen Exchange of Saturated Hydrocarbons in
the Interaction With,.Sulfuric Acid,"'D.N. Kur-
sauov,,'V.N. Setkina. '0. D. Ste*rligov- Inst Org
Chem, Acad Sci USSR
Iz Ak Nauk SSSR, oKhN, No 6, PP 1035-lo42
Investigated the exchange capacity of H atoms
of n-heptane, n-dodecane, 2-metbylpentane,
3-methylhexane, 2,2-dimethylhexane, 2,2,3-tri-
methylbutane, and 2,2,4-trimethylpentane in the
interaction vith deuterosulphaTic acid (I).
273T12
Found ,~~at O"Ily hydrocarbons that biLve a ter-
tiary C atom are capable of 'this exchange, and
that equil is established within several hours
0
at 20-25 . Also established that the highly
mobile H atoms of alicyclic hydrocarbons with
tert-C atoms are exchanged for deuterium on con-
tact with 1. State that the results check with
data subsequently published by USA investigators-

L~-_qydlro a C d
91, Xc ia o of _L
sulftj act 1_0~ N
winny And A, 1, , I'Ou
Khil,v Auk 19S4, I'V- If,; cf. C.A. 40. ex-
C 1,~- t r; Av~
ge uf Cyclic 11~ ill th,-,t;-t !ilcv bf
If.'so, "-.t,; Culall, The 0-It vXamI44v jS ~ Ill
alill the 44JUA. it
telllji. ill A ft;w linsi. Nt, (!x,:N:mgt- IA--, 1-1,to! t0th Ci,
r;ats tonlI4 of vi
-aid (
later n.ta. C'u'lo,oiddiv It;. twil.,21,tv.
cychtfivville.
so't mw(, vloifj:~r d,wi cyclop'..21. w U'lleft 11w C-4.
Al It atow, ar,~ I
ikco im"

All

eldfudw br m4m of d4o~
111. D. N. Ictirmacy Z. N. Patties I
All I
O
W
t
r
ns
.
rt.
Ak
r
t
k S
S
R
M
d
A
d
U
S
S
Mi
.
.
a
.
u
.
.
.
oscow).
.
S
.
.;
'
8 G(W
A
k
54
4
C
A
8
-
.59-0
im. Sau
. 4
l
10
, cf.
.
5, R., OhN, A
,.
'
Melc; C(CI1HCv)COCfI1CH,%O,jt)mC x P- Q
-IftiLting
~JC.11,8404tf- rietdcd metc. C(Cmurt)COM. CrIA(C. b1 i 4-
Pi~3.5 mV 1,473S, dio 0.9709, Thiv on qvIiUdom wt
uo. (cf. c.A. 44, 9107i) pve
'!
5*
112-12
u
4779
I r
b
0
w
(1)
?
"
.
.
, 4 a
o
,
il
.
,
1
j
c1
m
th
f D
11
b
I
d f
t
d
Z
hl
h
-
u
or
e s
u
w
c
t w3a t
en use
m
y o
te
7
Jim contact with H 8%) extriched with D; almost no
I
fiance was -b-X
M with this cyclic ketant: and a
stdt was obtatned In a
tiriftir treatineut of th
Imil
r r
j
c
a
,1
&
th
d
f
ft
Th
(4
4
L
te
W
44icnonc.
c
&ttcr
.
eaft
t
g.)was
t-lni
an- 4.4 C
DA a hil
at
pre d I from 9.6
v
AM

1
:
.
,
,
f,
batompermal -
-1 .
.
-nized Y1
elding IICWf and Fighcr erg. acids, tile rafter
id,
tion
6d
tthtswith
O
, in.
x
%
o
12"*
id
hkh
cr
. cu.
. w
-etatte
retained the *me amt
A tatch-
of D om the e
dk L
14
.
.
y
atj~m for the qatati(jim Is prewted which is consistent -
M. Kcso
wit athe v(PO, resulb. Z.-

If
AID P - 1118
SubJect USSR/Chemistry
Card 1/1 Pub. 119 - 1/5
Authors : Kursanov, D. N. and Voyevodskly, V. V. (Moscow)
Title : Some new data on hydrogen exchange between organic
radicals and Lone
Periodical s Usp. khlm.,, ?J, no
Abstract : Hydrogen exchange of
cations Is reviewed.
exchange of carbonyl
a table. One table,
Institution : None
Submitted : No date
61 641-653, 1954
free organic radicals and of organic
Experimental data on the hydrogen
compoun4s with D S04 are compiled in
38 references (1j Russiant 1934-54).

'4'- Rautloas of hy&qfa e=hw4e of saturated kat(Ads with
CCU$ M, U. Kursanoy and V. N. SetidnAL (N. 0. ZeUn*4
last. OrgM%W721FM7W. USS.R., Mweaw). Dakl4dy.:
;Ak4d. Mak S.S.S.R. %. 69-MI954).-D-11 exchange was
studied ks the serf,,% of satd, Aliphatic ketanes In mas con-#
'taIaIn01tSO,,aM.HgPOtenrkbed with D. TImfollawfus,
exMilft of exchaute. rapo[w " percen"n of exchAnp 0d
tall a41 Atoms In the kctoats, wm found: in wm'~
in 'DIP04, hfecollu - 100
, .3. cycloMtszoae L04.9, cyclo-
hexabone IWO- "ne prod that the exchanpd D ato=s
were located in ct-porritions ms had by treatment of the D,
eichanzcd ketones with HzH y(elding the dib=Al deriv%,
wbich were devoid of X) content. The ttactions In DtSO~
-i I hr. at room temp., those in D,PO, for 48 hr$. at
u.
r
tpodbirup- U.'CAALS51f. G. U. KOSOIQPofr.,-t

Y D. H.
USSRAhemistry
Card
Authors t Lavrushin, V. F., Kursanov,_R.._~_' Mamb. Corres. of Acad. of Sc. USSR.;
and Setkina V. N.
Title I Reaction of'aaturated hydrocarbons with sulfuric acid
Periodical 9 Dokl. AN SSSR, 970 Ed. 2, 265 - 266, July 1954
Abstract : Exner'imenta showed that saturated hydrocarbons absorb light in the range
of very short waves thus indicating that the curves of their sulfuric
acid solutions owe their origin to hydrocarbon-sulfuric acid reaction
products. Since the absorption curves of hydrocarbons are analogous to
each other and with the absorption curves of trimethy1carbinol it becomes
evident that the nature of their reaction with sulfuric is also identic-
al. It was also proven that the particles, forming during the reaction
of hydrocarbons with sulfuric acid, aro identical. Six references. Graph
institution ! Acad. of Se. USSR, Inst. of Element. - Organic Compounds and the A. M.
Gorki3r State University, Kharkov
Submitted : March 24, 1954

KuR!~A~_NTUV D"Istry - Physical chemi3try
Che
Card 1/1 1 Pub. 22 21/48
Authors Kurasnov, D. N., I-Iemb. Corresn. of Acad. of Se. USSR.; Setkina, V. N.;
Title and Byk
I About the intra-molecular effect of nositive-charged centers on the
proton mobility of H-atoms
PorlodIcal I Dok. AN SSSR 97/5, 835-838, August 11, 1954
-Abstract- __$__TN,_effect of -positive ;-charged- centers -on the - proton- mobility- of--hydro-
gen..atoms, is explained. The difficulties involved ~n studying thp
eff6k"t of a tri-covalent positive charged (oxonium) O-atom on the pro-
ton activity of H-atoms, are discussed. The results of the hydrogen
interchange reactions are shown in tables. Four references: 3-USSR
and 1-German (1933-1954).
Institution :
Submitted : April 8, 1954

'j N-H Group
(Sluchay zamedlennogo vodorodnogo obmena v gruppe > N-H)
PERIODICAL* Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1958, Nr 12, pp 1493-1494 (U3SR)
ABSTRACT: In this brief report the authors mention that the isotope ex-
charge of hydrogen in the NH-group of dimethyl carbet~oxy
pyrrole takes plac3 comparatively slowly. It turned out to be
possible to measure the kinotics of this reaction at diffevent
temperatures. The velocity constants were calculated by a firet
order equation. The experiiaents were carried out at 12, 15, 20,
and 250. K 12 = 3.2.10-5 K 15 ~ 15.6.10-5; K20 - 1-07-10- 41
K 25 = 2.21.10-4 in see- Apparent activation energy - 25500
The retarded hydrogen exchange which took place in this
case is interpreted from the viewpoint of the theory developed
by A. I. Brodskiy. There are 2 references, 1 of which is Soviet.
Card 1/2

SOV/62-58-12-18/22
~he Case of a Retarded Hydrogen Exchango in the > N-11 Group
IASSOCIATION: Insti-tut plemen'. oorganiche ski kh soyedineniy Akadem-ii nauk SSSR
(Institute of Elementorganic Compounds, Academy of Sciences,
USSR)
SUBMITTED: May 22, 1958
Card 212

/V 6!
.91 UT111 OR S: Vol i,in, Li. Y- S. D.
2 1 TLE The Influence Ex(,,rtLd the NucL.-o,-,1A1j.a of t"., A!Acln U-,-on titj
M.Aur(~ of Linka,,;e in J.'ropilium Corpoundo
~miona nu khara':Ler ov'~Izi v ropi li~-"
PERIODICALs Zhurnal 011)31,clhe~r K11-&-iii, Vol- 28, !~L' 3-)u ~33 (Ujj10
4
A3STRACT: A number oi' jalts of th~~ nro-iiatic c-tior c.' c,,'c1o'1-.c,)'6-,1trJ--
onyl (tropil-4um) w-j rccently -roduccd (rcfurunc~~o 1 :to )). '.",iu-
are all oalts of suf.-L-ic-icrtly s t r on ~~ ac i d 3 (x = C 1 J , C 10 ,
PtC1 61 B(C6 H5)ip NCO). On thi. oz~ier hand tiv, ;~I'L'th-
oxytropi-litim, ropilium cyanicie, trrpiliu-.;,.Lhioet1hcr 'r,21*-r,~nceol
Lilid 21 ) I wb a rc the X i -- z-n L n i on o f ji: f f i c iri t I,,- -.:, i : ac iJ s ,re
cov~,Jent coi.ipoiuida o ` t~ I(I I) . !" I t"I"r '.'Ie zattilo, leave
I Ile 112rC :ill" kill-'
open thi: Al:e3tion wltet'ier the covalent ,os-
jes3 ;. c--clohelitatri-mo- or norc-,(!-Jcr;c struc-,ure (cf. r--fcrcnce
ie aiAhorj iaulz~ it Vicir Lak LO 6('tC!'.'iJnU the ;'10rL thc
1
ioni-c co,ipound C H +X tranoforns into thL cov co-i:,ound C H
7
7-oje 'lle" tile 7 7
-d 1,2--ix,~tive:3 of
-X. or thio pur,-
-) , A:, iell the
Licetic L-0. bc=oic -.(!id:j 01*L. - 1.'[~.iu
tropilill.m acetate uj t'l.. tropilill,'I L-::'.Ct!J t`w c,-'clr,-
Card 1A -b,2r;:-,o!0;e) ~Irr)-"'.d to "').- t'!jC .11.~-

The Influcncc j%'lii0!l UI~Oli t'llu liotvl-,: 0i'
in Troiiliwa Coi.,irwund.3
I u j ic ..,!1b 0 iv k, din n('11 olar
tv..il-,,.iLion I-rom tliQ icnic ~:,ilt,; o--' t".01,11li-6-1 LO i':_' UU-
v~-Iunt dLriv.',d VL,3 liQJ ill Z'I.. int~.!.'V~-j j: Q~ coi7rt3.;*,,oi,.,!il-..
--~ (,- j., r
s . Tho ~--, rt- Lo a
-,7e L, Ci u d t 0- - D
tlt-~t tho trol-Piun icn bellav,2~; in .. ~kr li::" t'l-
roacts ziccordir , t!ic --du-c 'F
c H + 2H 0 c H OH i- It 0
7 7 7 7 5
211C th- a3jii...~,,Aicn t*....t -dOi
'~ C. (), t j 1. 4 1:
0 L I 1 1; CL 1. tditI
1 7 :5) t d pi 1 i 11:1.
~111 ti j f i r. I L
Cl or, 01, trc-
0:.- ulc;~,illll 'CIUIC'
L d
C 3 it l,*Gr C. L, iorle. c n ~;o,j 4
cr-
'14]~,, 00 C'I
:IQ,r4 cf C, t i C.-I 0 o;:i,lc
A
c I ..rit') ccrru.--j.cn.'in.l ;:ctic -~l k,
o2 t-.t':cr
- `1 ~ V,.- L.-4LQ
4; 1:
Grtaaco. The 1:1.0duce
Card rc%cdon of' ti-piliui pclc'~Icr--t, :3 1; u ia

Tli~z. InfluQncu '.Sxurtcud J,y the J%ijjCl,~Oj)jjjjja Of t'j,- %liioll U",~,.i, C.- .:-Llll:~, U!'
in '2:Cl.'iliULl Co::ipound
acc-tatc in and in ~-lcGllel wcl.~: it
pojoibl.2 to produca -otao-sium
Wunzoate ard tropiliuz:i purc;~.lorotc in rci- b. ,.,i
action of oilvor benzoitte cmul LrOj)ilillil ill, .lCc"-iUl 01'. ni-
C!] lhQ irjjtLljjjj~y Of L~L CjClo:,,.-I_tri_
trot-,ethane. This indicat L ~ k,. 1) "
Cnyl uther unu t1lu inclim-tion tO AlL ~!LValel-f C0.1-
pound C 11 -X in tropilium cyanide and P,'IYI
,.rovL d107 be con;jijerably utabler. It is j.?lt0rC.Jtin;, L,:-'t 4.11 th~2
1
acid pvoccuL; o - the li~drolyois o~ tropilitu.,, cru,-A~c iso-
L.ILlYiZit'Lioll supposedly takes place ur:,l that tic uc-41-1' -;L!
formcd. Conclu:3ions: 1) Tropilivu accLatc, -ba,~'zoate Z.1;~ C.-l-clopen-
tadi(,,rjlc,,rclof,,L!ijtutrlene which larovod o '..e cov,,lent co:!joundj -.,(:ro
;,ruduced. 2) It wis ohown th,,A t'.e nuttire o' lin':LL - I
J. -,a o!' the CrCli)-
I:,.c1tatrienyl rcuidue with t1he --nion depend3 on the nuclcojAiilia
cf the :nion. The tr.~.-juition frul,l iollic to covale;-It tro:~i1ili'm (10-
riv-Lilics lici in thu rzin:-e of K frc:i 1.2,110- 110 li.-,r,).10-5
3) It vaj ullovrn that in thu cl~ljc Of -Lin acid k- d ~ID l': ji.3 U.' t IV Di -
lium c'anidc witb the foz:latioll of p"
ro u p i n hcnjl-c~~tic ,.,cid
Card 3/4 tLL!:cs plLcc. '41lieve are () rcferericcu, 2 of .re Slavic.

7(-:-2-10
'2he Influonce Lxertod by the :41clooploilia of tilt,
Anion Upon Vic~, L'ati,,.t',
in --'ropilium Coupoundu
2. J --'CC L.21 011 zInstitute fOr Mc;:iL!1tal-organic Compounds AS WSR
(Ill,;titut
3UILII'22:0: April 15, 1957
AVAILAM: of Con.-ross
Card 4/,~

71
/2 o.. I 2o-4 - 311
AOTHORS - Setkina, V. if., Ktirsainov, 1). N., (brre:;-pondinf-, Member,
Academy of
TITLE- Hydrogen Exchange Reactions of Alkyl Chlorides With Hydro.
chloric Acid and of Tortiary Butyl 'Acohol '.'-'hen the 'Hjdroxyl
is Substituted by Chlorine (0 reaktsiyakh vodorodnogo obmena
alkilkhloridov s solyanoy kivloto.%. 1 trotichnogo butilovogo
spirta pri zamene gidrulcoila na klilor)
PERIODICAL: Doklady Akademil nauk SbSR. 1958, Vol. 12c, Nr 4; up, Bol-8o4
(US'qR)
ABSTRACT: The reactions of tPrtiary aliphqtic n1cohols witft a saturated
HC1 solution proceed very rapi(JI:, and practically irrev-rsibly
under the formation of Ftlkyl chlorides. Reliable date on the
mechanism of thii reaction gre lacking in publications, It
might be ansumed that thp mentioned reaction proceeds accord-
ing to the carbonium-ion-meohanism, The authors attempted
to decide whether in connection with it an Pxchange of hydro-
gen takes place . They have found thqt the numbrr of hvdrogen
stoma exchanged for do~uturium corre3ponds only to th,, number
Card 1/3 of n-hydrogen atom,3. For this purpone the reaction of tertiary

~_-C)V 2o-12o-4-31/67
Hydrogen Exchange Reactions of Alkyl Chlorides With Hy4oRloric Acid and
of Tertiary Butyl Alcohol 'When the Hydroxyl is Substituted by Chlorine
butyl alcohol with a saturatod. HCI. solution was investigated.
The solution was enriched by deuterium. The rapidly formed
tertiary butyl chloride containcd onl,,- a sm--Il amount of
deuterium. During a further contact between chlo.-Ide and
deutero-chloric acid this amount incr:-ased (Table 1),. Other
tertiary chlorides behaved in the same way. A primary alkyl
chloride, that is to say, butyl chloride did not enter the
reaction under the same conditions (Table 2). Numerous in-
vestigations (Ref 4) of the mechanism of various solvolylic
reactions of tertiary halide alkyls showed that a)l these '
reactions proceed according to the S N4-mechani2m. Their veloci.
ty is determined by the ionisation velocity of tertiary
halogenides. Obviously the mentioned reacticn with deutero-
chloric acid is a special case of oolvolytic monomolecular
reactions. Thus it may be concluded that the initially men-
tioned hydrogen exchange reaction of tertiary alkyl chlorides
is connected with their capability of being ionizable in a
IICl solution which as is known has a high dieiectri.- constant.
The result of the ionisation of chlorides is their hydrogen
Card 2/3 exchange. The phenomenon that only Cr--hydrogen atoms of the

3OV/2o-12o-4-31/67
Fy!rogen Exchange Reactions of Al~yl Chlorides With Hydrochloric Acid and
o.f Tertiary Butyl Alcohol When the Hydroxyl is Substituted by Chlorine
chlorides take part In this process can be explained by the
impossibility of migration of the carbonium center alon '- the
hydroc6rbon atom chain. This is inpossible becauce of an
electrostatic attraction of this center by anions or as a
result of the influc-nce exerted on the carbonium carbon V,,.
the solvate shell. In this reaction the carbonium ione are
either not formed at all or they are so short-lived th9t they
have not enough time to be exchanged for the acidous deuterium
donors. The first assumption is more probable (Ref 5). There
are 2 tables and 5 references, 1 of which is Soviet.
SUBMITTED: February 21, 1958
1. Hydrogen--Exchange reactions 2. Allkyl chlorides--Exchange reactions
3. Hydrochloric acid-Exc1,'umge reactions 4. Butancl--Chemical
reactions 5, Chlorine-4hemical reactions 6. Substitution reactions
Card 3/3

AUTHORS: KursA=L, D, N. , Bykov,-% , Ye , V, SOV/62- 58--7--2/26
�-e-tkina, V. IT.
TITLE; Hydrogen Exchange An the Process of Heterolytic Reactions. Zz-
change of Hydrogen Atoms by the Substitution of Iodine in Alkyl
Iodide(Vodorodnyy obmen v protgesse geteroliticheskikh reaktsiy.
Obmen atomov vodoroda pri zameshchenii yoda v yodistykh alkilakh)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1958,, Nr 11, pp 8o9 - 813 (USSR)
ABSTRACT: In the present paper the results obtained in the investigations
of some reactions of the nucleophylic iodine substitution in
alkyl iodide are described. The possibility of using the reaction
of hydrogen exchange in the study of the mechanism of hetero-
lytic reactions was investigated. Furthermore the hydrogen ex-
change was investigated in the following oases; a)In the hydro-
lysis of tertiary alkyl Iodide by water enriched with heavy
hydrogen (deuterium), b) In the exchange of iodine atoms in
alkyl iodide with a 56c/4 H J enriched with deuterium. It was
found that the hydrogen -change in C-H bonds occurs in such
Card 112- reactions where according to the data supplied by kinetic inves-

Hydrogen Exchange in the Process of Hetorolytic SOV/62-58-7-2/26
Reactions. Exchange of Hydrogen Atoms by the Substitution of Iodine in AlYyl
Iodide
tigations they take place according to the monomolecular
mechanism. It was shown in detail that the hydrolysis of
tertiary lodides(C 419j '-,nd C51111J) and the iodide exchange
In tertiary iodides are accompanied by hydrogen exchange
reactions, if the hydrogen ec:hx-~,p does not take place in the
reaction of the iodine exchange ii, secondary and primary iodides.
This tends to show the bimolecular mechanism of these reactions.
There are 2 tables and 30 references, 15 of which are Soviet.
ASSOCIATION: Institut elementoorganicheskikh soyedinemiy Akademii nauk SSSR
(lustitute of 4jemenzal-organ4.~ Compounds,AS USSR)
SUBMITTED: February 5, 1957
Card 212-

62-58-3-15/io
AUTHORS: Kursanov, D. 11. , Baranetskaya, 11. K.
TITLE- Benzylpy rid in e--If~Cyc lopen tadi eny li de ( A(-benzilpiridiniy-
-11-tsiklopentadiyenilid)
PERIODICAL: Izveatiya Akademii Vauk SS5R,OtdelcnVv Khimicheskikh Nauk
199n, Nr 3, pP. 362 - 363 (USSR)
ABSTRACT: Three representatives of a now class of bipolar compounds
(which contain a negatively char.-ed cyclopentadienyl Croup)
were already earlier described by the authors. It was now
interesting to synthesize the above-mentioned compound,
where (in con6'rast to the ilide) the ammonia nitroEen is di-
rectIj connectea with the negatively charged group. On that
o(.-:Lsion the same method was employed which Lloyd and Smizum
employed in the synthesis of piperidine-cyclopentadienylide~
The compound synthesized by the authors of this report pos-
sesses all properties oimilar to the ilides (see the diagram
on absorption in the ultraviolet spectral region. There are
Card 112 1 figure and 5 references, 2 of which are Soviet.

T- Ben ZY I Pyridine-111-Cyclopen tadienylide
ASSOCIATION: Inotitut elementoorianicheskikh
';SSR
(Institute fbr ElemenjMa,. or~;anic
SUBIMITTEDi October 12, 1957
62-58-3-19/30
soyedineniy A!Kademii nauk
Compoundal AS USSR)
Card 2/2

/Y
Uri
79-2-25/64
AUTHORS: Parnes, Z. It., Vitt, S. V. , Kursarov, D. It.
12ITLE: An Inveatigation of the Isomarization of Pinacoline by the Method
of Traced Atoms (Is3ledovaniye izomerizatsii pinakolina inetodom
mecheny'kh atomov)
PERIODICAL: Zhurnal Ob3hchey Khimii, 1950, Vol. 28, Nr 2, pp. 41Q - 413 (USJR)
ABSTRACTs At present different re3earcher3 found that the aliphatic carbon
ions (iony Izarboni,-a) enter into a reaction- of hydro,~en exchanre
with acids. The hydrogen atoms are exchanLed with the carbon ato~.io
clooe to the carbonmntor (referencea 1 - 3). It Was U130 0110VITI
that tho carbon center of the carbon ion which vaj formod by tho
action upon carbonyl compounds by sulfuric or another st.-on- Lline-
ral acid (at 0 0C) is incapable of miaratinG, in contruat to the car-
bon ion which was obtained from thc hydrocarbon -aith a tertiary car-
bon atom. Thus in 'the interaction of ketones , 41dc"hYdej, carboxyl-
ic acids with D 2S0 or D PO the hydro!~en exchznLe only takqs jklace
in thooe hydrogen dtoms Kai are at C . But caues of kctonc too-
.werization are k=m (references ij - 71 w1-.ich are evlali6d by a
displacement of the carbon center. Barton and Pcrter (refurence 6)
recentlymst exactly proved th-at the oxy,-,en ---Lcm dok- s not --o over
Card 1/3 from one carbon to another in the ketone i=.,Y_,ri,_.,afion, but that

71,1-2-23/64
An TrvestiL;ation of th(-, Isonerization of Pinacoline by th,~ Eethod ')." '-"r-:--c.3d Atc-nz
only the hydrocarbon radicals mi-rate. For confirming this situa-
tio~ they used ditertiary butylketono (III) which contains c14 in
the carbonyl -roup. It oeemed intereotin,', to the authors to inve.';ti-
6ate t1he interaction of pinacoline (V) with deuterosulf uric acid
under the same conditions tinder which the isomerization of the
above- men t ioned ketones (reference 6) takes place. The iuo:_ierizu-
tion of pinacoline assumed in this connection cannot be determined
by the usual chemical rieathods, as the reaction product is not dif-
ferent from the initial pro6uct; but by means of labelled atoms it
was 'hoped to discover it. On the basis of data on the re-rotipin.,
of pinacdine wish the fact that
(reference 9) it must be roclkoned
the ion (VII) dither only exists for such a jhort time that it
cannot i,iarkedly enter the hjdro_-en-ach"n~;e r~uction aziLi that the
regroupin,; takes place synchronously, i.e. without forraing a free
ion (VII). But the ions (VI) and (VII) OUSt eR3ily Linter the hydro-
L;cn reaction. Due to the reversability of the ioo.'rrizzation react-
ion all hydrogen atOM3 Of pinacoline ~iust finally be exchaiir;ed.
On the baoij of the data j~iven it nay be oupposed that the hydro-
,,en exchange in the hidden 13orierization occurs aj a consequence
of a regrouping of methyl ~;roupo and is inGepcndent of the displace-
ment of the carbon center. Sumniaryt 1) "%L interaction of pinaco-
11
Card 21;' line with deute-rootiYuric acid was investiL;ated under the conditions

7~-2-26IG4
An InvestiCation of the Ijoierization of Pinacoline by the -Let!iod of Traced Ato-1:3
of tho "etone iaomerization. It vvia ohown VEt unler those condi-
tionj ninacoline exchan-es tho hydro,;on atuouz; in the tertiary bu-
tyl 6-roup u~;ainst deuterium. 2) The mechuniail oL' thc reaction of
deutero-exchan6c and pinaco line -i.,,o:.,e ri za t ion were investi,-.-,ted.
There are 1 table, and 9 rL~ferenoes, ,,~ of wideh are Slavic.
ASSOCIATION: Inititute for ElementAl-orpnic 'Compounda AS U3311
(Institut u lo..wn too r,;-mic )iuj'X:'h :JUJ,.L:~jjC1JJJ A!mdeiaii nauk 366R)
SUBMITTED: Januury 16, 1557
AVAILABLE; Library of Con~;ress
Card 3/3

SOY/ ?o-12o-3-26,/67
AUTHORS Kursapov. i). N., Correrporiding Member, Academy of Sciences,
R , Vollpin, M1. ip.9 Akhrem, 1. :4.
TITLE: The Reaction of Tropylium 6alts With Vinyl Ethers and Mezcury
P-Chloroac4taldehyde (Reaktsiya soley tropiliya s vinilovymi
efirami I 0--kh1ormerkuratsetal'degidom)
FUIODiCAL: Doklady Akademii nauk 1958, Vol. 12o, Nr 41, urv- 531-534
( U~'~1'111 )
ABSTRACT: A aharacteristic property of the stable aromatic cation of
cycloheptatrienylium (tropylium) is represented by its ca-
pability to react with nucleophilic reagents. (Ref 1). It
was to be expected that the electrophilic property of the
tropylium cation Is sufficient alao for a reaction with more
weakly nucleophilic reagentsi as vinyl ethers. This actual-
ly was the oase, as the tropylium salts reaft with simple
vinyl ethers in aqueous or alcohol solutions even in the
coid under it uelf-heating. This high reactivity is a result
of the influence of the electron-donor ether groups Compotinds
Card 1114 with isolated or conjugated double bindings, however, Without

3 0 Vl;b - 12 0 - j -;--; 6 /6 '11
The Reaction of Tropylium :3alts With Vinyl I-I'thers and -ercu.y
acetaldehyde
activating subntrinct's (".i. for example, methyleyclohexene,
cyolohi-ptatriene atid orhers), or with electron aocepting
,glibstituent.,3 (cinnamic acid, itcrylic acid, acrylon-itrile,
chloronllyl and others) do not react with tropyllum salts
undor identical conditions. In till cases tile same nroduct,
res0ta independent of the nature of' the anion of the initial
salt of tropylium (whether bromide or perehl:)rute) Pnd Inde-
pi.,rident of tile cha-racter of tile alkyl in the vinylRlkyl ethers:
cycl,)hFotatrienyl itcetaldehyde. Thig reaction is analogous
to that of tile addition of mercury f?alts to vinyi ethers
(Rof 2)~ Therefore it could be aaonmed that the mechanism
Of intpra!,-tion of thp tropylium nults rith vinyl ethers includes
an a t t ELO iipon the double binding of the vinyl ether by tile
j on C H At the qaine tlme, or ~!iibqe-uently, an action of
7
one mollcule of' the t3olvent (water or alcohol) tctkes place.
i,.n acetai or n ~jemj--acotal Is probably tile Intermediate prod-
unt of' the reaction. The reaction velocity with the tropylium
galta is markedly roduced at tile transition from the .9imple
vinyl. ether to tile vinyl acetate, This apparently in conneeted
Card 211 with a Dartial withdrawal of electrons by the C-0 Froup.

SO-f2o-12o-3-26/67
The Reaction of Tropyl.ium o'alts 71ith Vinyl Ethers and Mercury P-Chloro-
acetaldehyde
CycloheDtatriene acetaldehyde was also obt~-ined by a counter
Syllthe3i3; that is to say by a r-~actinn of the tropylium
salts (bromide or perchlorate) with -mercu--y 0-chloroacet-
aldehyde. Because of an exchange of an Fe-atom Arith P. tropylium
radical an aldehyde was produced, which was identicxl with
that produced from vinyl ethers. This iz the firot case to
be investigated of an interaction of organomercury compoundq
with tropylium salts. The reaction of the tropylium salts
with mercury 0-chloroacetaldeliyde proceeds according to the
type of C-Plkylation. The haloid acyle 0-acylate mercury
P-chloroacetaldehyde. There are 4 references, 3 of which are
Soviet.
AS',)OCIATION: institat elementoorganicheskikh soyedineniy Akademii nauk
On.,iLltute ol'Elemental-wganic 'ompounds A'j II.;3R)
Card 3/4

SOV/ 2o- 1 2o-3-26,/67
The Reaction of Tropylium :;alto 'Nith Vinyl Etherij and Mercury fA-r,'hl(ro-
4
acetaldehyde
I
!UJBIAITTE,i), JaIlUary )A:, 1958
1. Tropylium. salts--Chemical*reactions 2. Vinyl ethers--Chemical
reactions 3. Mercury compounds (organic)--Chemical reactions
Card 4,1ij

SIVKINA, V.N.; KUnSANOV, D.N.
reactions of allq~l chlorides and tertiary butyl
alcohol, when hydroxyl in replaced b7 chlorine,with hydrochloric
acid. Dokl. AN SSSR 120 no. 4:801-804 Ja 158.
(MIRA 11:8)
1. Chlon-korrespondent AN SSSR (for Kureanov).
(Organto comoounda)
(Hydrochloric 'acid)