SCIENTIFIC ABSTRACT SKVARCHENKO, E.A. - SKVARIK, V.P.

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• Collection: Scientific Abstracts
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• Sequence Number: 20
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

04
/O.SgE~-~Idh 1= h
d. it
dou bmdo. R. Ya. . V. R. Skvwcbeniw. H. G.
Tresbchova, and V. M. Tatevsbl (Mosv6w State Univ.).
f. Gm. Chm. U.S.S.R. 20.44"1950)(EttSi. tm"ktion).
-Ace C.A. 43, 5W. R. M. S.

SMACHENX0, V. R.
-in'A
S t 21 ?26
J-3-
L- (35
C"T
11, 9 r)pi C'tV,,,e:MT-ClT--.)Cl Pr(l rt r-yture -f cis-
16
60
'D
/7. /7'1
; b- ( -, C:1 -
1.3 2 Lfreed frow 7~lnrtu 1~ 'r
rL
n n se r1 ,f,pc tro.,, 1y
d" 0-99R2,
isoT
i r Etgn tho lsi,Fil m-liner an- givf, idert-ical cirod'-!rtg,
0 6 Ro Sterv.

MARCHMO, V. R.
R. Ya. Levina, V. R. Skyarchenko, E. A. Viktorova, V. M. Tatevskii, and E. G. Treshchova,
"Synthesis of hydrocarbons. XI. Partial reduction ct diene hydrocarbons with a
conjugated system of double bonds by sodium in liquid amnicnia." (p. 690)
SO; Journal of Genaral. Cbem:istr , ( Zhurnal Obshchei Khimii), 1950, Vol. 20, No. 4.

SKVARCH&IiKO, V.R.
Synthesis of alkenes and alkynes with a central position of the unsaturated
link. Uchenye Zapiski Moskov. Gosudarst. Univ. im. M.V.Lomonosora No.131,
167-248 150.
(CA 47 no.19:989) 153)

R. V&. Levine. V. R.
cbe . and T. 1. Taubywye. t'salmik M*Aw. Unir.
a. No. 2. &f. Fie.-Mde. i. E&Vswm. New& No. 1. 137-8
(1931); cf. C.A. 45. &IV.--3,&-DkbIunx7dopwttm (ob-
rArml by chlminsilban of ryckn"Imliene Irt #U)% yiehl).
1% 33'. bw 50. wV I AM. dl* 1.311M. wkb MeNghr gnvv
:.Iu% nAwd c6-trams forms of
I.--, 7-IL", mV IAMO. 41:- 0.75W). G- M. K~ IPDII

Synthailin of hydruwllc;"~ XIVIIJ. Madtattim of the
411"Gan Wtweea tirgw"~14WSUJ COMAP"IlDillf Alld 1.4-
dichlorld" of wal - W dwall hydrocarbons. It. V
LeviltA mid V. R.Turch"Ay (jUtiscow StAte Uitiv.21-
lltjjnik
,Nauk No. 3. 91 cf. C,I. 43 3WV- 46, M.Sh.
.1954e. 1W.Se.- -Addil. of -99 S. (CIC11,61L)"t. NNIgur
ffriorn ',j g. JIrBrj in a N at- and %tirring IN firs. give &M
butarlicne (,-kbu-xtwd Ind recovered ai the tetrabrornide"'
while the org. layer. after being washed, F : v llel:inc
and .5"" 5-Arcent, NA 170'. mV L-1211A, d:* 0.7-11jl, which
ri'ld' 1), 119" "V .1.1, 1.31K1
.1 Aindl.(r traction willa IluMalir flkvvil~ icarr hatudictir.
:Iflvfc octane, anif 1G% 6.4tdriene, 1),i 95 fle, bTu 2(W.
1.1-135, (11, U.7571, yielding the dihminide, hs 127%
n17 lA%U, tl:* 1.3013. Raman analysis g,tvc the Ir-48
line, irOicating Mit the dWrcvnc hail tile transconfizuration;
tile prcence of soluc I-alkene was indicatIA by tile lol,
inten,ay MU) line; thii may be accuuntcd for by allylic
tFLMtllKFlHCnt 6f tile i(ItCMIC(IiAtC alk-clic trumi'dulidc.
Me icat-fiiin of llu- dichloride with R.NtgX is Im-lirvrd to
procevil by cleAv,igv of the 2 CI atoins. which, ill reacting
-ith 14LNIgX. yicid the twinned Uphocabint, Rt. %ith
g~zler.aioll of lintaditne; tl;r "aarimil- re~ctiuu i, Urgely
'upprv'~I. G. 11. Ko!,Lipuff

thesis of hydrocarbons. XLIII. Partial r ductfon
of%ne hydrocarbons with c,DnjugAtcJ system of double
bonds by 6 ditun In lll!dd ammonla. R. Yj. LgAnal
Skyarclicitko. V. N. 'osthl,
0" b~mik det
'e chdAff. P11. 355-61(1953); cf. C.A. 47,
12210d.-Reductinn by Na-NH, of 2,3-dimcthyl-J'3-buta-
diene results in addu. of H mahily (08-0%) in the 1.4.
positions, atid to a minor extent in the 1,2-positions.
With the unsym. diene, 2,1inethyl-2 4-fictitaillene, 1,4-
addii. predominates also (93-4%). T6K.NainBOOml.
liquid NZ'113 was added with stirring an EtsO soln. of 39 g. 2,3-
ditiiethyl-1.3-butadiene; after 2 hrs. the mixture was dild."
with MO. evapd. at room temp., washed and dried, yield-
ing 58% total reduction products, which were sepd. into 3 g.
crude material, b," 50-72.1% and 19 g. 2,3-dime1hyt-2-
hulene, b. 72.1-2.2% nV 1.4134, d-* 0.7077; the Ra~nan
%pectrum. of the product had a 1674 cm.-L line characteristic
of the above structure. Raman spectrum of the toterun
showed the presence of 2,3-d imethyl-1-hn ten e. Similar
reduction of 25 g. 2,4-dimethyl-1,3-pentadiere with Na-
NH; gave 72% reaction products composed of material, bT~'
81.9', n
0 1.4038, do 0.6917. whose Raman spectrum
5howed the absence of any contaminant fit the 2,idiffldh
Perdene produced (for comparlson a spectmen was . by
li rolysis of diisopropykarbinnt acetate; the product. brig.
Z14,20, "V 14072, do 0.0927, Raman spectrum gived.
Similar Na-NHj
-i;~iuctlon of 2-methyl-2,4-06titaillene boa
70.3% nIO 1,4520, do 0.72,00) gave 2 fractions: SMO
mr1hyt-3-Puentene, him 57.5-8.5'. YtV 1.8905. do 0. and
about 8% material. bT" 58.6-67*, which also contained gonfe.
2-rnethyl-2-pentene, confirmed by Raman spectrum of tbU
mist. fit comparison with that of i pure. synthetic spedmeti-.'
Ontn. of 1kfcCH-.CHCH:CH, (25 g.) with 30 IF. dry Mir
Wit
, .h cooling. followed. by adiln. of the crude resulting
bromide to NfelfgBr (from 39 g. MeBr) and stirring 1.5 firs.
lit the cold and. 6 Ins. at reItx, gave 40%fure I-MdAYI-&
peWene, bm 57.".5% tsq. do OAM whose Pituidn
spectritnt WLt Mt kivch in th~ paper; thd of the specimen
prupil, by Na-MI, teductlihi Is givift. Similarly, -24 e.
CH'-C"ledt. C11, treated wi-if dry J4Br "d the resulting
bromide tredied with Me?,IgBr gave 13 g. (43%) 2-MeJAYI-2-
PrMlene, bru 67% nV 1.4025, do 0.6019, Raman spectrum
M. KOSOIRP04
given.

411YI.Ydollexame. 61161-1,50, nV 1,45W d~~# 0.813J7 CrItanLIZI
-I)
fre
uenc
1641
42
Ar
ld
d S;
l1
A
Cf
d
(C
.
.
cm.
no
an
w
.
.
a
.
,
q
y
'
LIIIAI Now reaction 01, IetfAbYdrOPhlhAJjC
=de;
(Prodticls of diono sypillesis) with phospborus
Pentoxide. R*..Ya. LevMa,_Y__H,Sk chenko. N~ S.
and R. G. Treslich-
ur.. Wbshkof KhMi.- 23
1 1 1953); c ., C.A. 48,
9939c, 49, 829e.-Tbe reaction of arious substituted
v
tetrahydropbthalic anhydrides with P:O' d')cs not go through'
the formation of a ketene, andthe decarbonylation step is
simultaneous nith dehydrafion,. in which the a-11 atoms
,participate. Heating 20 g. 2,3-dimethyl-1,3-butadiene
with 35 g. citmoonic anhydride in C4Hs 9 hrs gave 3370 1.-
anhydride. b--s M-
7', nl~' 1.4790, d," L1052. This (19.4 g.) treated With 14.4

PjO& and heated gently, catered a- vigorous -reaction.
f
iemp. rose to 200'); the mLct. was then.heated to 290'
and Enally to 350', yielding a distillate of 65% pure 1,2,4-
Ir;meIhy!bcnVn,#,.b?i3 16S.5', W; 1.5030, dn 0.8770-, the
Raman spectrum also agreed with that of the pure sub-
stauce. No indications of.,mcsitylene,or V,2,3-trimtthyl~
hmzene were found. It the reaction went through the ke-
tf.qy stnge, the pre5erce of H atoms in the I and 2 positions
liftvr b.7en lwcemi-':try. KO~012poffl

d?nIhp%=uf hr(frorwhowi. XXXIX, The dicliffirlde of
taqi~tjv Ill the of -ne5 w th
A. S1 Ok-tille6ell, alid
__/ -
ji V, 1!47.
KItint. 23, 72.5_8(11133r~ C.-I. 15, Fi:15.f; -18,
Lowering of tit(: tenip. 'of elik-riTtation of
doe,.t not affect the "vicid of the priultict; cliloriwitim; WRS
livest run at -7.5' ill ibq. Fito mild the thcort-tical phi it)
%Vt. WIWI; reacht'd. and evapi, of tilt- olvitit gave 32j~' 1
dirhh,ride (11), bt, 80-1*, ill, mid aNo a Im-r-boiling
rr.,ction and 25% mjchimgrd 1. To RIc.%fgIIr hom 121) g-
hiefIr ill :300 sul. Ut:O wa '; ~" Id'-d %-ill) "Ooling :0 P., 11, and
the tnLxt. allowed to staud ~tirrvd l" Im'. at roolil
teml). atilt refli "C'd 2 It"., d-molm. %61h Avolf f~avt-
.10% 1 and 23% lin.,
n' '* 1.42715, d~ 0.7tI5, Aoe JUmmi pl-rilum
Cmiraftwd lite foll,min fine-.: 11VICO.
nw,: i;,
G79(10), 7-W(tf), 71.10~u ;,), SPI(IJ.). 90710),
912(0), (~)3-3(3.5), 97WI), 1018(ij,
107-45), 1170(1,5),
12.37~1.5), ul~soj'5),
1t;10(0.5) and Th'. It"M tilte im-
puritv of ill -eflivi,nic (frmll
12,3 g . Pri3r) with t7.5 F. 11 ~imiltrlt. gav-_- ,, le 1. 17(;'~
heya "t" Mid IM,, 5,';~1bwfhv1-5-f e, -11 1 -1.2',
n',? 1 11-10, (1p, 0_77.S2, Raman i~perfriiw (cm. 1) 2713,H).
:t97(f)'5)' -w)(I), 191(l). 522fl),
111MV0.5). i~71")n)), -;:i-%-0.5 7~111(1), 792D),
1) .7,), 87-11(4), 956(h, 999(ti,
0
105101 1% , 111_1~~l . . IO-SY I ), 1102( 1). 117190.5),
1 Vise 1 "0. L, # 1~ 1 1. 1:1)[k I_:;). VJOI(2.5),
HR~~' t i I.W 10'. 1 U5,t)(3), VWXI.5). and lf,6;'412~.
Vie :Wli; 11'~ I 1 011" adillixt. of all -ethylenic
hi'di- t'6011 have forimid ljy all 'ylie hift f lite
A;'!, if" O'l I ........ Cl livri". during tit,, rencti ... t.
I to (C[(:('11.1, itt that Owir

. 7
dichloride-s yidd t1u: -011%lulic by-prodllc(~-' with RN11g.N:
(C.A. 46, XL. Reaction of the dichloride of
cyclopentadiene with or gaeutaguesittinI-compounds. R.
ya~. l.evina, T. I -l'tuitsNreva, and E. G- Treslwhova.
lbill. '35 -j _'i
Et-0 was added with kc--NaCl cooling 3.5.4 g'. CI; dist..
gave 1350% dichlopide, CJJiCl- (presumably the 3,5-Cl,,
coinlid. although tilt! 3,1-anahir %night be pri'ent), b, 35*'
big 50'. n. d. 1.2 103. darkeiii in air and even in N.
Aluch high-boiling matter wass also formed. To McMgBr
(frorn 5290 g. MeBr) wasaddecl with icu-NaCl cooling 120 g.
of the dichloridt, tilt mixt. being stirred 3 firs. at rocan
ternp. ans: 4 lirs. at reflux. Dveornprit. with dil. AcOll
and distu. ovt-r Na gave 20% C7111-. colill)(ried of 'Ollie
130-70% 3,5- and 10-100/0 3,1-diaiethyliplopentene which
resuitea from allylic shift during the ir-uic'tiun. The mixt.
could I, t be icptl. into comporient%and the whole tint SI.-L3*,
Pill,* 1.42W, d_, 0-7614. The presence of the Raman line
at 1613 cm.-I indicated the cyclopentene structure with
Me groups not at the. louble !w-id. Themixt.hydrogeriatcd
over M-A1101 at 150' nji.crif I,Z- all([ I,xdimethyl-
cyclopentancs, b-.zi 89-5-90.5~, n2.0 1-4113, (to 0.74.~7:
the compti. of the mixt. was defluced froni known consts. of
the ingredients (Bazinilin, d al., C.A. 42, 623Si; Kazanskil
d al., C.A. 42, Similarly 1,'t.%[gBr g3ve 12~~
arixrd 3,1 ond L-,,, 1-10.3% 0.'
1.1391), (1, 0.71122 fit k suggvsted that tilt! suppo,cdly pure
3,5-di-EV'ricriv. rited by Muller and Hngli:sh, C.A. 46,
.1 mg, i4 a[so a imilar inixt.1, and 50t, 3-c1hyleyclopritlene,
b,. 97" n"" 1. ViIO' if, 0.792N (C.A. -17, 3248c). Pr,%Igl3r
gave apparently only 3-prop lry.,lopentrise (although scane
I-Pratialog mijilt have J)"Un iy,r,.-vn0, lyre t25 , 0,*, 1 4370
,1, O.P918, in 7% yidd. ,;,tell ;, pr"Inel call arise
b,rimili-m brumid", w:
Ile
ik-ld Owallo", 'mucli.d. G. IN1. K01i'l;LjWff-

IAVIH,ft. R.Ya.; SKVARCHWNKO, V.R.; KATAYEVA, H.S.; TRESHCHENKO, Ye.G.
-
Synthesis of hydrocarbons. Part 43. New reaction of tetrahydro-
phthalic anhydride (products of diene synthesis) with phosphorus
pentoxide. Zhur.ob.khim.23 no.12:1998-2001 D '53. (KLRA 7:2)
1. Laboratoriya organicheskoy khimii im. akademika N.D.Zelinakogo
Moskovskogo gosudaretvennogo univerBiteta.
(Phthalic anhydride) (Phosphorus pentoxide)

" D
q
S
thesis of h
lidroc bans. Newreg0lonott
0 e5 r."
Dh Ic anhvdr roducts oLdiane imittliefils)'-.-
Urtft-, It y1t Kevittit, V R varctenko.-
t1do5 in an ntneva. 'Dokk; Y,~Ak*d~-Msmh
.N.S.S.R.-OU. 95-43( On ydropt thalle anhydrides
11
heated with PjOj split off inles CO and 1110, forming aro-
matic hydrocarbons. Thus, 29 g. 3,6-ditnethyltetrahydro-
phthalic at;hydride (1) treated in the inolten state with 23 It.
P,O# and heated carefully to 110~201 re-Lcted vigorously
with beat evolution and distri. of the product (completed by
heating to 230-). washing and di5tn. gave 80% p-xylene, -
identified by oxidation to P-C4Ha(COH)j. Similarly the-
3,5-di-Ale ijonjer of I gave 60% pure m-xylene, and the 4,5-
isomer (11) gave 40% pure o-xylenc- Heating U with 10%
KOH, evalm., and acidification gave 4,5-dimclAylletrahydro-
P~lWic acid (111). decomp. 1.15% which heated similarly
with P%O, gave 809v a-xyteuc. 11 tmated with (try 1ICI In
abs. EtOH gave 7270 di-Fj ester of IU, b, 163* n" 14670
d3. 1.0450. which heated with Pj0# similarly jLc 3i%
xylene, with CO and CtHa- G. M. Kosolapoq

SKVARCHENKO, V.-R-I LEVINA, R. YA., KOSTIN, V. N., TREESHCHOVA, rE. G., AND OKUNEVICH A. S.
Syntheses of Hydrocarbons. XLIV Partial Reduction of Diene Wdrocarbons with a
Conjugated System of Double Bonds with Sodium in Liquid Ammonia, page 355
Sbornik statey po, obshchey khimii (Collection of Papers on General Chemistry),
Vol I, Moscow-Leningr~-.d 1953, pages 762, '166
Moscow State U, Laboratory, of Organic Chemistry imeni Acad N. D. Zelinskiy

USSR/Chemistry FD-1246
Card 1/1 Pub. 129-8/25
Author Levina, R. Y&; Shabarov, Yu. S.; Skvarchenko, V. R.
Title Hydrocarbon synthesis XLTV. Formation of alkanes resulting from the
reaction of magnesium-organic compounds with un-saturated 1, 4-
dichlorides.
Periodical : Vest. Hook. un., Ser. fizikomat. i yest. nauk, 9, No 1, 63-67, Feb 1954
Abstract : Established that the formation of paraffin hydrocarbons from the reaction
of a Grignard Reagent with ethylenic and with acetylenic 4 4-dichlorides
is similar. The yield is dependent on the structure of the radical in
the Grignard Reagent, the normal type giving a greater yield than those
of the iso structure. One table; equations, thirteen references, four
foreign.
Institution : Chair of Organic Chemistry
Submitted : July 7, 1953

LEVINA, R-ya-; SHABAROV, YU.S.; SKVARCMIKO. V.R.
Synthesis of hydrocarbons Part 44.- Formation of alkanse from the
interaction of magnesium organic compounds and unsaturated 1,4-dichlorides.
Vest.MoBk.un. 9 no.2:63-67 F 054. (MLRA 7:5)
1. Kafedra organicheskoy khimii.
(Paraffins) (Kagnesium organic compounds) (Chlorides)

USSR/Cheritistry Synthesis
Card 1/1 Pub. 22 32/56
Authors I Skvarchenko, V. Levina, R. YA.; and Okhlobistin, 0. ru.
Title Synthesis of hydrocarbons. New:method of synthesizing 9YMM..octaWrcphenari-_
there (ocLanelitrene), 4,5-cyclopentanoindan wid their.hamologues.
Periodical t Dok. AN SSSR 99/5, 789-792, Dee 11, 1954
Abstract. t The reaction of splitting tetrahydropthalic anhydrides under the effect P~0~.
was used in the drivation of tricyclic condensed hydi~oca,rbons: By=. octzLby-~
drophenanthere (octanethrene), 4,5-cyclopentanoindan andAheir ho.mologues.-',,
The basic diene hydrocarbons-were found to be 1,11-dicyclohexenyl and
dicyclopentenyl, the first of which conbined with maleic,anhydride yielded',1.1
2,3,4,5,6,7,8-octahydrophenanthrene. Other hydrocar .bons derived from
dicyclopentenyl mixed with maleic, citraconic and pyrociiiehonine anh'dride's'-
are listed. Twelve references: 4-USA;4-USSE and 4-German (1873-19535.,
Institution The M. V. Lomonosov State University, Moscow
Presented by: Academician A. N. Nesmeyanov, July 16, 1954

V
,
2"

theils of hydrocarbons. Wail., ib.,ime
ipben-
"
a zenes from adducts of alkadi
ag to pyrocinchozilnic a
nhy-
-dride. - V, R. Skyarclicuka. R. Yn. Le in:l -rind 1'.
_ v
ostro Zhur. Obshche~ Rhins -3 t I

QEt

N
~!~
3fW84.
5414d. 50. _9440g.-
,

Heating 2,3 g. 2,3
-dirnethyl-1,3-butadiiiiie with 27 g. pyro- N

0

cinchoninic arthydride. (1) 20 firs. at 170-80* gave 90% -
Ph
1,2,4,5-ittrap)iethyi-1,1,3,6-letraljydrophihalt*c anhyttride,-.
2
'
*
5'
76
hi
h (30
d
) h
i 1 :1.
.
c
eitte
, w
w
th
g.
0.5 g. PIO~ tol
10
gave a
distillate which yielded 45% clurenc, m. 78.5-9*. Simi-
fatly Idind mixed 2-methyl-1,3-pentadiene and 2-metbyl-2,4- gave 1,141narbelbox
160% nIz? -1.4675, y-2,4-d-y&WOj#hj bilk,
d, 1-0087;-*W~W Us urea-and EtONa.
l
penLidiene litated 15 firs. to 140-601 gave 72% 1.2,3,5- g2vep In (fro, Vlo
iyWd- Hydrogeria-

icy Nj In the cold. in dry UtOl f gave 58
ti 9t
kiriLmeihyl-1,2,3,6-filrahydrophihiiiie `2 nhydride, bt.120% "l?
i li~iroJ2.41keplane, bir4h987-8.5% a JJ 1.4396. do O.S106,
*
s
firs, t i
Ach heated as above with P,05
t
1,4850 do 1.1037, wil
*
Z~ Raman.
ficitruin was:
295(1)i

', then to 200-330', yieIrIM 62% isodurene, b, 52
to I
. --397(2), 4&
387 1(1), 499(12),. 5M(0). WO-5), (71(0.5)
no 1,5120 (enide), purified by heating with al. W&OH and - -718(2), 786(3. j 830(2.5). 890(12), 9.53C30). 970(1). M(--

disin. in N.L Pure isodurene, in. -26'. to -24 , b, 70A-1 * 10220), 1641:4106(l), 1227(25)~ IM'O--N 20 ,
( ) ' 13520);
XLIX. Spiro 12.41 hepta- 1382(2.5), 142712). 1440(lo)-, 1440jr(2).. Treatment of thii
1,3-diene and splro[2.41heptane. R * Ya. avina, X. X
_
i with Hg(OAc)" iii filo readily cleaved Cie 3-membered ring
Mezentsova, and 0. V. Lebedev. I
id, 109771100; d. and treatment (if tile product with aq_I.Br 4%1.(2-
CA. 48, 6972c.-Reactiou of 115 g. (CHjBr)j with Na: branionierct4ritlhyi)cyclopeiltanot, M. 70*4 in J. Geg.
deriv. of cyclopentadiene. (from 40 g. cyclopentildicne ard Chem. U.S.S.R. 25, 1051-3
1055-7(1955) (RujI.-tranga-
28 g. Na) according to the previously described technique tion).
G- lkf- 'C

(loc. cit.) in liquid Mi. rave 25';Pspiroj2.4jhep1a-1,3-dienO '.
(1), biec 57% nif,1,5078i d. 0.&"9,-- Its addua wilk rwiek
anhydride, m. W (from pctr. etber), -1 (0 g.):adiltid-to;
-nemalonate, obusitied
Q114 soln, of monomeric di-E, t methyle

-and:
by thermal depolymerization of 12 g, polymeric, vkter'
the milit. refluxed 2 ho. gave N% 1,1-dicarbethozy-2-5-effidii-I
'
7
'
4
90
cyclopropylidelie-3-cyclaherene (11). bo 13841
, nw 1. .. . dil
f:.'
1.0879, which trea ,ted- with PhNj .yielded M_za 4 1
4
Hydrogenation of U in the cold over Raney IM ia MOIL I
dry

j.

etynthesls.d byn (00
I Cgelogentehyl. H a. Uvina V. R lk,~urcbenka and 0
lAq EXHOWITIO v bshzke
h71, 25i 140&9(IU,M S' a.-Reating 25 g.1
lj'-diftydroxybicyclop~iityl with M ml. 10% HtSOj 4 hr3
0-
at rcfiuxs2ve a mixture of I,V-UryclopeWenyl (1) and ip't
14,51-dec~n-11-oue (H), b, 75-90', coutg. 74.6% of the latter.
The Oxt. was heated with maleic anhydride and the ppt.,
se!pd.;. yielding pure 11, b,* 8(14% nj? IAMD' do 0.0899"
(2,4-dinitropheny1hydiarone. . m. If the diol, le
heated 2 firs. at reflux: with almuinosilirate catalyst, asimila
FnLxt. coutg.85900 ketone h obtained Thediol(100g.),300.
AcA treated with 3 g. coned. H,~O' in so g. AcO (prepd,
g
.&y previawsly) and stirrcd 5 firs. at 42-5* then quencliedi
I m
HO and truated with Na%COJL gave after extu. with MO.
and scpn. of the suspended crystals of the diacciate of the,'-
dial, 50% 1, b. 78.5% b. 77-5-9', nV 1 Z268. do 0.9259, and
M.8% 1.1'-diltydraxyb,,'cyclopentyl,diacetfile. N 120-8*, Tn.
114,,~iagu of the diacetate at 480* ovex glass*
wool in N brave 70% 1. 11telluxing the dint with Ac-.0 5 firs.
gavc7-41"01. llydrORL113601 oflover Pi black gav.1100'N
li~yd.1-e,ilyl.b,=t-*Z..,'.)zi'l.-IC,1,5,d~0.8m- C. A
M-K

-.1- ~
T...
-Al~--,- -,
-1; , ~
-

k'ez-

Synthesis of jlidtoiarbon's.' LVII. Partial reduttion of
-
diene hydrocarlib-h3-w
UE-a-c6njugited system of double
bonds. by.ineans of o u In H id -R. Ya.
'u u
so'
=
R-

-
1, amIr,-
v
q Nt n~,
i g

I i1 T tME t i o n),g
c.A-sij.927
j
,

SLVAqCEOWKQj-V.R.; MIMIN, M.G.; LEVINA, R-Ta.
~Cts of diene hydrocarbons with diethyl ester of azodicarboxylic
acid. Vest.Mosk.un.Ser.mat., mekh.,astron., fiz., khim. 12 no.3:169-174
'57. (MIRA 11:3)
l.Kafeclra organichealroy khimii Moskovskogo gosudarstvennogo
universiteta.
(Hydrocarbons) (Formic acid)

sKVARcHENKO, p.R.; LEVINA, R.Ya.; CHERVONEVA, L.A.
~
Synthesis of aromatic hydrocarbons. Part 6: Hydrocarbonu of tetraline
and naphthalene series. Vest. Moskl. un.Ser. mat., mekh., astron., fiz.
khim.. 12 no.5:177-180 '57. (MIRA 11:9)
l.Kafedra organicheskoy khimii Moskovskogo gosudarstvennogo universiteta.
(Tetraline) (Naphthalene)

1-~ -f,- - . - 1-1 - -I- 4~
-. . I I --
SKVARCHENKO, V.R.; LEVINA, R.Ya.; KUZIMIN, M.G.
Synthesis of hydrocarbons. Part 60: Ethyl benzene homologues
prepared from the adducts of alkadienes with methylethrlmaleic
anhydride. Zhur.ob.khim. 27 no-7:1784-1787 Jl '57. (MIRA 10:10)
1.Moskovskiy gosudarstvennyy universitet.
(Benzene) (Olefins) (Maleic anhydride)

5(3)
AUTHORS: Skvarchenko, V.R., Levina, R.Ya., SOV/55-58-5-28/34
_6~ e-r_v'_o-_ ~ le-Va',~~ - 1 - -.-A , -,
TITLE: Synthesis of Aromatic Hydrocarbons. VIII. Alkyltetralins
(Sintez aromaticheskikh uglevodorodov. VIII. Alkiltetraliny)
PERIODICAL: Vestnik Moskovskogo universiteta, Seriya mittt~iatiki~,, mekhaniki.
astronomii, fiziki, khimii,~ -.1958,Nr 5,PP 187 - 190 (USSR)
ABSTRACT: From adducts of isopen and 2.3-dimethyl butadiene-1.3 with
the anhydrid ofal-cyclohexendicarboxylic acid there was ob-
tained by heating with phosphorus pentoxyd the 6-methylte-
tralin (47 %) and 6.7-dimethyltetralin (59 %). The anhydrids
of 2-methyl- and 2-3-dimethyl-,n~2_octalin-dicarboxylic-9.10
acid and of the 2-methyl- A2-octalin-dicarboxylic-9.10 acid
are described for the first time. - There are 10 references,
4 of which are Soviet, 5 American, and 1 German.
ASSOCIATION: Kafedra organicheskoy khimii (Chair of Organic Chemistry)
SUBMITTED: December 28, 1957
Card 1/1

SOV/51-5-5-9/23
Aa-aa Sea-I-_z)ring Spect-ra. of Hydroc~_rbors of Vari-lus Types. V. BAUL-Ln seal.-.arin-
Spect-1-6. of Vlar-c--Ain Bi-Space and Tri-~;yclic Diane Hydrocarbons
_Iai~ian spectra of 2,21-dicyclopant"anyl. and of dicyclopontadiaae wore
ob-Lainel using a class "ShtvnWhal," spactro7raph, as described in
I fs 1, 2. 'ri,- Ramnn spectra of 2,21-dic,,--clolhaxanyl (Fi& I curve vi,
Re
1,11-dicyclohexauyl (Fig 1 curve a) and of 1,11-dicyclooont3ayl
(FiD 1 curve b) ware obtained using a tripla-prisia glass spectrograph
ISP-51 with photoalectric recording. Table 2 gives the values of the
Raman fr3quencias and in-t;onsiti-3s of all the five hydrocarbons.
Raproduci )i1ity of '%,he results 7nas satisfacrory and the differences
batmeau individual ineasurawant's of tha strong linos did not excey]
1' 3~o' (a 5a Fig 2) . Tha r3sults obtainad are discussed and intarprat-ad
iii detail. As part of the discussion the aathors quota the G==G
frequencies and intonsitias of various diones with isolated avid
conju,galled doibla bonds (Tabla 3) Thera are 2 figures, 3 ta-blas and
12 raf-3rances, 11 of vthicla are Soviet and 1 Gar-man.
SUBL,=AD: D3caubor 31, 1957
Card 2/2 1. Hydrocarbons--Spectra 2. Roman spectroscopy 3. Spectrophotometers
--Perfirmance

SKVARGEMKO, V-R-; IUINA, R-Ya.; CHXRVOMA, L.A.
Synthesis of aromatic hydrocarbons. Part 8: Alkyltetralins. Vest.
Mosk.un. Ser.mat.gmekh.,astron.,fiz.,khim. 13 u0-5:187-190 '58-
(MMA 12:4)
1. Kafedra organicheskoy khimii Moskovskogo gosudarstvennogo uni-
veraitetik.
(Naphthalene)

AUTHORS: Levina, R. Ya. Skvarchenko, V. R., Chervoneva, 20-118-5-2-5/59
--- I r
L. A., Fedorchuk, L. V., Vasi ly-6va, T. T.
TITLE- The Synthenis of Aromatic Hydrocarbon.,;
(Sintez aromaticheskikh u&rlevodorodov)
A New Method of Synthesizing Hydrocarbons of the Fluorene
Series (Novyy metod sinteza uvlevodorodov ryada fluorena)
PERIODICAL: Doklady Akademii Nauk SSSR, 1958, Vol. 116, Nr 5, PP. 938-941
(USSR)
ABSTRACT: The effect of phosphorous pentoxide on tetrahydrophtalic
anhydrides leads to the formation of aromatic hydrocarbons
with elimination of CO and H 0 as was proved by some of the
authors (referencE--1-6). In ?he present paper the influence
of phosphorous pentoxide on phenyltetrahydrophtalic aldehyde
(I) (an addition of phenyl-butadiene with maleic anhydride)
was investigated. In this case the reaction lead to the
formation of fluorene (with a 21% yield) instead of diphenyl
as might have been expected. It seems that the reaction
passes through intermediate stages of an intramolecular
Card 113 acylation of the benzene nucleus. This leads to the foramation
The Synthesis of Aromatic Hydrocarbons. 20-118-~5-25/59
A flew Method of Synthesizing Hydrocarbons of the FlUorene Series
of tetrahydrofluorenone-carboxylic acid (II) which is further
decarboxylated to tetrahydrofluorenone (III). Under the
influence of phosphorous pentoxide this is changed into
fluorene. The authors simplified this reaction by starting
from phenyltetrahydrobenzoic acid ( an addition of divinyl
with cinnanic acid (V). When it was warmed up with phosphorous
pentoxide fluorene was formed with a 63% yield. Prom the
addition of cinnanic acid with isoprene and 2,3-dimethyl-
butadiene 3 methylfluorene (50% yield) and 2,3-dinethyl7
fluorene (53% yield) were produced. The production of just
3-methylfluorene (melting point 87,50 - 880C) and not of
2-methylfluorene (melting point 1o4oC) which is isomeric to
it, from the addition of isoprene with cinnanic acid confirms
the structure of this addition as 4-methyl-2-phenyl-1,2,3,6-
-tetrahydrobenzoic acid. Prom the addition of cinnanic acid
with dicyclohexenyl (VIII) and dicyclopentenyl (IX), 1,2,3,4-
-dicyclohexane-fluorene M with a 83,5% yield and 1,2,3,4-
-dicyclopen 'tane-fluorene (XI) with a 73% yield could be
produced. Thus the reaction of the 2-aryl-1,3,6-tetrabenzoic
acids (addition of diene-hydrocarbons with cinnanic acid)
Card 2/3 with phosphorous pentoxide can be recommended as a new

Aromatic Hydrocarbons. I;,. Synthesis of the SO1r/?0-29-?-17/83
Hydrocarbons of the Indan Series
LL
7cre synthesized in high yiel'o (Sc-ert7~ 3) af ter lon-rar hea'in-
in t-he autoclave. D'y causing the anhydride (I) to react with
phosphorus pentoxide indane (11,r)(69%)(Scheme 4) resulted. From
(II) 5-methyl indane (V)(61%~(Scheme 5) resulted by the save
method. 5,6-Dimethyl ipdane VI)(8,',%) -was obtained by caucing
anhydride (III) to react with phosphorus pentoxiee (Scheme 6).
The hydrocarbons obtained were determined according to the
constants and melting Doints of their oulphonamides. Also the
compounds (VII) and (VIII) were obtained from the anhydride of
1
Ad -cyclopentene-1,2-dicarboyylie acid. These adducts were
transformed by phosphorus pentoxide into the PDlYCYClic aromatic
hydrocarbons (IX) and (X)(Scherie 7). There are 17 references,
7 of which are Soviet.
ASSOC IATIO'-,,T: Yoskovskiy -osudarstvcnnyy univer3itet (!~oscor, State University)
SUBLUTI"ED: JulY 4, 10,58
Card 2/2

SOV/79-201-8-33/81
Skvarchenko, V. R., Levina, R. Ya., Karpenko, N. F.
TITLE: Aromatic Hydrocarbons. X. Synthesis of Polymethyl-diethyl Ben-
zenes From Adducts of 3,4-Diethyl-hexadiene-2,4 With Maleic and
Alkyl-maleic Anhydrides
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 8,
pp 2605 - 26og (USSR)
ABSTRACT: The aromatization of the tetrahydrophthalic anhydrides under
the action of phosphorus pentoxide carried out previously accord-
ing to the scheme
110, + I EIC 0 ----) 0 0 P20 + 2CC, + H20,
G:10 01
was used in the present paper for the synthesis
diethyl benzenes hitherto unknown (dimethyl-, trimethyl-, and
tetramethyl-diethyl benzenes). The transformation of the adducts
ef tetraalkyl-butadiene (of 3,4-diethyl-hexadiene-2,4) with
Card 1/2 maleic, methyl- and dimethyl-maleic anhydride under the action

Aromatic Hydrocarbons. X. Synthesis of Polymethyl-diethyl SOV/79-29-8-33/81
Benzenes From Addacts of 3,4-Diethyl-hexadiene-2,4 With Maleic and Alkyl-maleic
Anhydrides
of P205 was investigated. The behavior of 3,4-diethyl-hexadiene-
2,4 in the I'diene synthesis" has so far not been investioated. It
was carried out on heating in the autoclave at 12o,13o, arid 1goo,
respectively, within lo, 2o, and 3o hours (yields 72-41 and 67'/"")
(Scheme 2). From compound (I) compound (IV) was obtained by
heating with P20 5 in a 71% yield (Scheme 3). By reaction of P 20 5
with (II), (V) was formed (89%) (Scheme 4). The adduct of 3,4-
diethyl-hexadiene-2t4 with dimethyl-maleic anhydride, compour~ 'Mr)i,
was more resistant to P 205* Compound (VI) could only be obtaincd
by heating the reaction mass for 10 hours (Scheme 5)(77c~). The
synthesized hydrocarbons not yet described were closely charac-
terized. The initial diene, the 3,4-diethyl-hexadiene-2,4, was
obtained by dehydration of 3,4-dimethyl-hexanediol-3v4 with acetic
anhydride in the presence of orthophosphoric acid (50-54%). There
are 11 references, 6 of which are Soviet.
ASSOCIATION: Moskovskiy gosudarstvennyy universitet Woscow State Uniltersity)
SUB11ITTED: July 4, 1958
Card 2/2

5.3400 77347
SOV/79-30-i-8/78
chen-k u
AUTHORS: Slcvgr levina, R. Ya., Pugina, M. I.
TITLE: Aromatic Hydrocarbons. XII. Adducts of Alkadienes-
1,3 With CL-Naphthylacrylic Acid
PERIODICAL: Zhurnal obshchey khimii, 196o, Vol 30, Nr 1, pp 46-50
(USSR)
ABSTRAM Heating of CL-naphthylacrylic acid with excess
butadiene in benzene in the presence of hydroqu1none,
in an autoclave at 150-1600 for 30 hr yields
2-( CL-naphthyl)-1,2 3,6-tetrahydrobenzoic acid M,
(yield 27%), mP 113 6. The same reaction with 2,3-
dimethylbuta-1,3-diene at 180-1900 for 14 hr yields
4,5-di.methyl-2-( CL-naphthyl)-l'2'3 6-tetrahydrobenzoic
acid (II), (yield 53%), MP 156-1586.
Card 1/4

ArDmat,lc Hydrocart:)ns. XII. Adducts of 77347
I-1-1-t1h (1-111aphthylacrylic SOV/79-30-1-8/78
Ac id
butadle-ne .u,_Lth cinnamic acid) which in reaction with
p205 eliminates water and yields fluorenta. The ob-
tained a-( A3-cyclohexenyl)-naphthalene was Identi-
fied by conversion Into a mixture of CL--phenylnaph-
thalene (VI) dnd CL-cyclohexlnaphthalene (VII)
(by heatkin,,, With Se).
M (V11)
The authors %,;i;3!i to
absorotion siDectra.
and 5 references, 2
U.K. re~erence3 are:
Card et a!. , J. Chem.
tharil., L. A. Kazitsina for the
There 1.1, 1, table; 1 figure;
CD
Soviet, 2 U.K., 1 Gerrrian. The
Coolk., J., Dansi, A., Hetiett, C.,
1191-35, 13_19; Cook, J., Haeiett, C.,

I I A d' (I t ~3 77
A a.,,J
A id
a i,.T r i c e S I
State -,.Tn-, ve, si ty gosudarst-ennyy
universit'et)
De-!ember 19~~8
a - d

77-,~48
307/79- 30- 1 -9/78
AUTNORS! Cq-jervoneva, L. A.., Levina, R. Ya.
TITLE: Aromatic Hydrocarbons. XIII. Synthesis of Fluorenes
1?-1,o!,i Adducts of 1,2-Indenedicarboxylic An?iyd- -4 de
PERIODICAL: Zhurnal obshchey kJi-11-rii-J, 1960, Vol '~,O, Nr 1, DD 50-54
( "'T S S ~Ez )
ABSTRACT: 1,2-Indenedicarboxylic anhydride was used in ',-,-his
,-,,ork
, for the first ti~ie as a dienophile. Ethyl ester
~-tydrocmna-,1.ic acid laa3 the starting material from
U
p-:',!-ich 1,2-indenedicarboxylic acid (I!, yield
nm 215-217 0) and it's anhydride (III, TieId 4315'
0)
-;---~'-185 were -.-neuared tllrou.-h t~)e forma~---on of
ol,oduct-
1,2-indene-
ac'd (I), mp-

7~n
C. at
y C

A C '[;0rj:3 .XIII 'Synthes is
Add:ucto cf 1 21
An'hl,,dr ide
J!
011~' CO'
"CO
co
77 348
CIO
V/79--_30-1-9/78
to
ell:
Both anhydrides (IV and V) were not described in
literature. The adducts r1 and V on heating with
p2 05eliminate carbon monoxide and water and
ield (7%,) compound VI, mp 123-1240, compound VII
eld 76,1~,), rkp 128-128.50-, and compound-VIII
M
(yield m0 158-1590.
Card;

~I'Jjo
A a t Ic ir -1 t,r)-C a i- I) orij .
XITT. S,r~
o -71,uo2:~e!les -7--o- i~d~!ucts of
er~ a rb o-
Ind-
A S' 0 C Ir7 ! 0
7 7 4' 8
SOV/79-30-i-o/78
There are 6 references, 4 Soviet, 1 German, 1 French.
State Un?~.versity (-M;os'l-lovs:,1--4y gosudal-stuvennyy
lianua--,y 22,
Ca---d 41/4

77 3 111 ( 9
10
1i) V/`_,'9-30-1-lO/78
A UTi [OHISI: Slkvarcheriko, V. R., Chervozifi-va, L. A., Puchnova, V. A.,
i na, Ya . .
TITLE: .,'~romatlic Hydrocarbons. XIV. The Reaction of Phosphorus
P~-I'-C'~-*- - "It
U 1-h Adducts of Dienes, arid 4-Dihydronaoh-
Acid
PERIODICAL: Zhilrrizal olisfici'aey Ichimii, 1960, Vol 30, Nr 1~ PP 54-59
(USS"1)
ABSTRACT: The t-ollo!.Iing adducts of ",11.-dihydronaphthalene-1,2-
d_-Tcarbo-"v1_-`c acid v.,ith butadlene, iso.prene, and 2,':Jl-
di-.r!le'~-hv-.,bi-i'L-.a-l,'-diene were prepared: 1,4,c),10,11,12-
_.:,,C~i,o,,)hei-ianthrene-11,12-dicarboxylic an-hydr-de
(H) (,,,,iold 4o,.z',), br) lt'DO-l'-(Oo (l min); -jl-methyl-1,4,9,
l' _12-1-lexahl,droo' enanthrene-11 12-dicarboxylic
10, 1 -11 -
anhydr-lde, (III) (yield nq) 1 "12-141 .50 (not
and
anhydride
Y 2.,d 7221_1~' M,-) 'T' -77
'0S1D'_:c'4vely. adducts
C~~ r d of anhydride

s c he ---,re
:71-~ _,C

Aromatic Hydrocarbons. XI-V. The Reaction
of Pilosohoriis Pentoxide With Adducts of
Dienez: and --~,l~-Di-iydi,cila,)h~ulalene-!,,~-1-
dicar't)oxylic Acid
Ij
I
M
Card 4/6
77349
ZOV179 -30 -1 -10/78
(X 1)
The adducts V and VI are stable toward P 205; heating at
,,oo-4oo0for 10 hr resulted only in formation of
na!-jl-itlialetic--1,2-dicarbo,