SCIENTIFIC ABSTRACT SICHENIKOV, I.A. - SICHEVOY, P.S.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001550420009-5
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: March 14, 2001
• Sequence Number: 9
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

--",T 7A ~ec 'I Vf,! 11.110 ~;ur--ery Clct-
6210. PRIMARY CIRCULAR SUTURE OF THE ARTERIES IN INFECTED
WOUNDS (Russian text) - S i c h e n i k o v 1. A. - KIHRURGIYA 1958, 6
(98-106) Tables I Illus. 3 ' -
Experiments were carried out on 74 dogs; 62 experiments with administration of
antibiotics and 12 without antibiotics. Arteries were sutured mechanically in 35
cases and manually in 39. Primary circular suture in suppurating wounds gave
favourable results in the first group. Best results were obtained if surgical treat-
ment of infected wounds was carried out within 24 hr. after their infliction. The
results depend to a great extent on the rational choice of antibiotics, based on
analysis of the wound microflora. Mechanical suture has considerable advantages
in infected wounds over the manual suture. The results of these experiments make
it possible to recommend wider application of primary suture of arteries, even in
conditions with pronounced inflammation.
Z

Fj
HA
ix 'a'
6 - 0 1 -91. NR
78
va 3

SICHENKO, V.K.; I-V&OV, B.V.-. POLYAKOV, I.I.; "XztllKOV, A.A.;
IZ.RA---LIT,
DOPF7.Wl) G.A.;
E.M.; NOTYCH, A.G.; TOPYGIN,
L.A.- CHALYYI, G.Ya.; STETSENKO,Ye.Ya.,- UDOVICIIENKO, L.V.;
FILIPPOV, B.S., nauchn. red.; LERNER, R.Z., nauchn. red.;
GOLIDIN, Ya.A., glav. red.; KULESHOV, M.M... red.; POLOTSK,
S.M., red,
LIPI-product cokfi iWilllit.1-yj Kokfiokhtmicheskoe proizvodstvo.
M09kva, Netal."Lurr,lia, 1965. 1C-17 p. (MRA 18:7)
1. TSentrallnyy nau,21mo-130le,l':)vaLellskiy institut in-
formiatsii i tekhniko-ekonornicheskilch issledovaniy chernoy
metallurgii. 2. Direktor TIzentrallnogo nauchno-issledava-
tellskogo inot.itut-a dnformats-.i i teklipiko-ekonomicheskikh
issledr,vaniy ~hernoy metallurgii (for Kuleshov).

Synthesis of poeudoconhydrins. U Synthesis of one
isomeride of racemic 2-propyl-5-hydiosypiperidine. I
Swill and J. ,;letter C"Ur'll"m
14. : It, N 1, Ilk .4
,lilt (ImIllig 11%. 0. m it..
d .,Ikvll,% I 1.111w, mid I'll"10m. .."k 1.
I'd it. P, I
p'. I
73 1 r.". I P
aci-I (111,, in I I ~-'
mid .1-prolivlji.pyriilone-5-carl)oxviii icid, in.
III I'. Ikearbiltylation in Wiling I:tcO,ll K.Ivv 2.
acid. in. 129-111'. which a~
cmiverted viA the Et ir,ter. b., 1:15 it'. ImIr.m4le. in, lot)
I '. .'side. mul urethati. in. -I)'. it)
41111r. N, 1:14 -d' (pirratc, in. lilt , 1. Dusull'atioll yn-IlItA
in. 9t 2'. which hi -
dr.)IC.-flatc.1 (Pt cm,ilv-t) I-,
I 1111;~ It'll, md O'Sol. f-."..1 .:;,I
Irk, ml..~Ou ".0.1 ."..1 11'.1 it., ~ 'I., 1. .1 Ill
I I Il.kill IV % I I Ihv '1116.111, " 1.1 I'l
virl-l" b0ift lh~Av 'Still

-CO"Ill M do GMWNMdM of P-W&*b~SwO cmwtde
with nukkumft aiied I M. SrobadA.
Gut. and F. f1ratift (Tech. Univ.. Pracim. Czeeb.T
C". Lity 46. 51-2(1962).-An ether ecilu~ WO ml.)
omits. UZI g. P-0~NC4H.COCI (1). 8 j. Clf,(CG.Et)., and
I - 13 tg~ Na in 10 W. RtOlf woo *Uawad to stwW 4 days at
MMI frull. . awn "Atil with dil. IfsHO.. tivated with
-\'~,C(N -In- mad evapd.; a " pd.. m.
MrOll'. susustviS to be (PAh.NC4H&CO)tC(COj 1). or
lwfh.il- fP-Ch.%CJtoCOXp4XhCAWOo)C(CO#Et)- w-As
A)jin"l in yfeM. AckWyft the! Na.Cf.)j cit.
'PI'll 2.45 X p-(,),NC4%COCJI(COAt)v. m. 43~5'. Simi-
;
kar rvartion occurried birtween 1 6 C. and No cyano-
amiati, (firmn 3.3 S. ail the ewer) wid gave 4 X~
CU),C(CNC(),%fr in 153-4' (from Meolf), Safi 1.7 g.
#-bvvc.jl,cOclR.v),COoMc. m. 157' (hcim MeOll),
ul- cobtained in 35% ykid firons EtOMxClf(CN)COAfe and
1. hil. fludlickf

SICHER. J.; FARKAS, J.; SORM. F.
Studies in the chleramphenicol series. Part 4. 5yathesis of
henyl)-2-hydrozymethyl-2-dichloro-aestanldo-1,3-propandlol
in English with summary in Russian]. Sbor.Chekh.khim.rab.
f
105 F '53.
1-(p-nitro-
and a correctioa
18 no.1:102-
(MRA 7:6)
1. Chentral Chemical Research Institute, Pr w 9.
(Chloramphsaicol)

LXWormwpheakcd serks. V. Analop containing CW-
flue In the side ~kajn and cumiles. AA and-la
C J.-Z4,Tfl, l1r.30, A-fUKUL),
lv~
49. 218b. Vt. Steric comse oftlic red=tjon, of de-
hy4rfwhInramphp"l-, mad related compound3. jifisicher.,
Afir"lay 4vo Afandalma Hrd j2dxu-dtmmt-.tmtf
n Naw 'Ibid. 4
&
144k ~tZm (C=h. 87.
G.A. 49, 219b,

S
- ~q, j. , j.
Sicher, J., Farlms, J. "Studips in the chloramphenical series.* V. Analogues containing
chlorine in the side chain and oxazoline3. 1). 552 CASOPIS PRO PEESTOVANTI P-kTEKATIKY.
GZECHOSLUVAK MATHE,~,UITICAL JOUR-ITAL. Vol. 47, no. 4, Apr. 1953, Praha, CzechoBlwakia.
SO: Monthly List of East European Accessions, LC., Vol. 3. No. 1, Jan. 1954, Uncl.

J. and others
Sicher, J. and others "Studles in the chloramphenicol series." Vl. Tile steric course of
the rediietion of dehydroeblorarmhenicol -and of related compo,.mds. o. 565 CASOFIS PRO
PEESTOVANI MATEMATIKY. CZE(;HOSiA)VAK MATHB,-LVTlGAL JOURNAL. Vol. 47, no. 4, ADr. 1953,
Praha, Czechoslovakia
SO: Monthly List of East Nuropean. Accessions. LC., Vol- 3. No. 1, Jan. 1954, Uncl.

SIGH~&R, J..,,, SVOHODA, M.- FARKAS, J.-, SORM, F.
Studies in the chloramphanicol series. Part 7. The side reactions
in the reduction of dehydrochloramphenicol Lin Inglish with slammary in
Russian]. Sbor.Chekh.khim.rab. 19 no.2:317-329 Ap 054. (NMA 7:6)
1. Department of Organic Synthesis, Institute of Organic Chemistry,
Czechoslovak Akademy of Science, Prague. (Chloromyeetin)

"JtLui_;_~O on the Series. V j.-)L:.eTTnsaturate(~ derivatives.
Tn English."
(OLLIUCTION k)F CHz,~ ',-.L CUA%UINTIC.~UuNJ. 3f,0ffl4!K Hw H1, V T
ij KILEf
-t.-.'uT, j _a
3, June 195~, Praha, Czechoslovak-;
"0: !,:nnth--',-y List of East E'uropean iccessions, ~LzItL)' LC, Vol.
N"o. 5, 1955, '-.',nel.

--!1e, 1 It

41. Ill, .... ..I
(F a-ld
r""'MO'l -"'HCOCIIO' Clf!sif tfi"~ iN 'tc-
th, - .,I: ~". .4
~ -1 f pharril:,ccl. tcs!g "f tile chlornaud
ast:d~; ~; -4 gi%cit. Ad.ling
A. P "J;"; I I '.F 12.12 p. r---O:NC0 rCO-7 iO I-
~'o 11-0. C~11;. 111tcling liw
fonu C'Ff! iriv,- 13.31;
tIV). Ill. 122"
vol- dioxmie
L-9 r.
W). lit. ),$I- (Irctill diox-me). In
jWLV,4. j;-O~NC&II,COCII(NI1Ac,-
c: I.,A,-, 143-l' Mwil EtCkll.), i-1 72% yi,,II. Dktg.
6- viiit. "".79 g' 17. 70 fill. ;111d 4.0-9 9. At
ul"J'T Llic-i'lur if), I11.0-
min. a, -~W, c%tK. ith MM, di:!4. OfT Ow hclvrnt, noid
'~'YqK. the hon! I-10d vi~flded 2.03 g-. (64%)
rplh: C-P-' f,C! i(of 1)(-; 1. S: Q C 11 CI')-S.C 11, (VI), its,

132 TJIQ c'lwc coolp't. mai obtained In 10",/v yield by thr,
Rrflu\ingV1(1.2Sjr.)
C,11. ~5 ml.) with 1,52 g. p-.M~WLSO.-C'I and 2 ml.
j\f-TI; 2 hr,., chig. thr mixt. with '~'O ml. Et:O, filuring off -
tile salt, it"! and adding petr. cth~r to the
gave 0.55,
lit. 1,18, (fien? Moll).
.15.7 g. V ,W, :13 g. M 2 lirs. with .181)
lilt. CAla. devompg- the residue -xf(t,.r off tile solvent
.i:ha Mg, tartariclicid ia If0ml 11,10, heatingthc

mi'l 10 miTt- at ro" dilg~ "ith ':e& ~d.
1, 1. g.
"117 (from EM111- 17-m;- f-h litiniA A10,ol-II, ill--
2441 mi, 1111:~ Acolf (1-0!: 1: after cri-st,i.
7 1 f1mil PW TO
i;-;-P.MI;:1l lift'. ,I!t I
I1,,CI,Iiii,,i,,-d in 1-t-0;uItTlill.at
Cff-N:QC1ICI7).I-).CIf.1 (C.4. 43, :MIL-) (VIII) (1.51-1 g.)
it% ;ill. dw)-ittr-tv ;ddvil I,i UtP w:th if fir m
(I ild ~iftc r ~, min. ivif It 15 Fit I. AvOI!, I I - ,An~ v.l, I I. d w it It
I IF rev I!ortion-- If.0. f I ri-f I, ~ti!d it - prf. , iviih I 1 11-42 g.
th-r-r.; I.N('~I I,C-l [I Oll ",.- 1
1 1,; ~ (f-im -e Fit if I )~ 1--Omz ,I 11.-.5 g. IX ill b
Ill Fill-Nfetc~!) "ith a "J". it, If) 1111.
7,1f:0) Al."I R. Ill, ~,-h4 Y; Nk"! Off lei q-'o I -
Co,AICI~)CII--SI3Z, M. lill' (frOTT! Ftfl'-11~. A(71'11-latiOll of
VX AY) awl 11;~()j g;~vc 87"Y",
(X), In. (from MINJO.
Xill C~114-,ilfll,,L
;r -F PIS, 3 E;av
('17-)
IT 1!,-Tratov tl4iie lilt[
all
XALC I I 1. 1 M, C11. IXI), ?,. It! '-:I'
N.1II,:!.;,!, XI "o-'. 1 11.1. 1:1011 " I'll
VIs )!j , I oiw-,~ ow
Al~i
TtIF- 11~ n m ;if ~-11 .1 OT tlj~- It t, 110
1 6,
Uz~
it

GIN). llcarin,,~ lli~ nlit- (If (1~42 XII, In nit. AJ,111,
ml IS in). 11,C) ;!u mill. en till, stcam Imth Imzlcr "I"
ml. 114-1. filtering tile twhid ~,lu. iia, C,
and evapg. tiv" 11111.1(v in -.,;(:Uo~ vVe 11,0k~ R:. I. Ill. WS'.
fiv;Iting 0,36 F. XI will. at Ilk) in IA 1,1V !0,76 i(collf
'Iml (litg, tile with 11,0 jpVc 0.7.~ j., (O.Irl g. Ali-i-
If I'll R.I.:, iz~ VI( Itifil
IF456
T"? ull. SOCI, I ~t, Ill 4, diog. ifif 16 $t ,)CI! m uvisul~ owl
cryAg. the t~,i )~lr frolil Cdl I, Raw! ;`i,wl g, ep'thm'j, O'dNIC',
fluxilig 5,35 Mit with 50 JTJI. BU01f 4 fits, ~tdd di-Ag. nff
tile Ilit(Al viddvd 1.25 K. fit-CO
(,NIIco(:IIclj)cI!,:;Bz, In- 16.1 Omni, rROID. Rc-
fluxing 4.45) g. erytis,--I-O..NC.)I,CltC]CII(NtICOCilcii)--
CIF-013/ (XIV) Wl mill. ill '.!fl ml. dry collidim! (Ml') 4lid
filterifIR ofT the c"lli'lific hydrcOlloride flcf~,-;ited ;Lft(.r the
of Elf) vivld~J 2.9
m. 12L'-I' (froal FU011), Ro-

T--o,W* synthe as of -cham&=&-ni
d. C.A. 49,. Mir.-A general synthesh of 1,4,74ridlkyl-
asyknes has been worked out based an the h)
of a suitably substituted ar-dihydroxyltenzosuberene w "e
satd. dial, midation of the dia[ to the coresponding III.
carboxylic acid, and cyclization to the desired exulene
slieteton. Chamairvidne was synthesized In this
2.3-(MeO)*C.H.CGCI and Pr.Cd gave 72%2,3-(MeO)A:Y.1
COPr (111,bo.t 104*; rcinir4rbowne, m. 154.5' (from MOHV
Refluxing 120 g. 1. Ot g. hfetNH.HCI, 35 g. (CHOL. and
2.5 mi. cened. HCI lit 450 mi. EtOH 4 Wit. with efficlent
stirring, adding 10 g. (CII.0)., refluxing 8 mom firs., distg.
off moqt of the EtOlf, stirring the cryst. residue several
times with EtzO. dissolving the crystals in H10, liberating
the bases with 400 mi. 10% NaOH, extg. the ndxt. with
Rib. Co=g. flie ~t. .-,a tucuo to 90 MI-and treuting the
concentr3te with dry HCI gave 66 g. 2.3-(MCIDNC4113co-
CTIEtCHINTMel.1-10 (U), in. 141* (from ELOII), and 05 g.
recovered L, Tm-tting-'11.5 g. H in 00 nit. 11.0 isrith 40 mi.
10% NaOII,:c%tg. the liberated hase with EtjO. adding with
coolitig 20 g. Afel, evapg, (lie excessAlel nad EtjO in "icua,
stirriag the crystals with IM tul. HROII, treating the inixt.
with NaCII(CO.M), 1preryl. from 2.2 g. Na. and 15 It.
Cll,(CO:Ft~j fit IM tit[. F1011, ra-fluxing the inixt. taitil
iv) more r.-calKA (M dkiii. off the MOII, di,-
~olvim; tioc N:LI in If.0, relluxitig Oit- criale tfft~tvr 2.11-
lith fit Itil. III",'
itccarl-Kylaling 111V (Ill-
i-j ifir
lit 2.3 X-*M,-f j 111 ~ FoLl I I C11-:
C 'i IT I'loo. ,61-ji~nl 2M j. III h.'
401 m[ ~A-rOlt ~-vr 3 at to 90' '!11.1; J:,
2 3
I Y, Ntill;: 251. IV lo. 11, 1 lit. Iti-411 '11111:7501; 14,11

Introductory remarks.
Ala,,L C1 ,1,
~s 2b, I'ag-;i
(1055)(in Euzl.).-A prograin for tile following ~;tries of
0, tiers on stercticheinistry of noncyclic coinpotinds is dis-
-rms am e7plained. 1.
played. atid th%: fundaniental tL
Steric course cf the acid-catalyzed cyclization of N-thio-
beazoyl derivatives of 1,2-amino alcohols. A new stereo-
specific reaction. jifi FarkA and jih Sieber. Clem.
Listy. 49, 1320-9; Chem. Collimlats.
20, 1391-1401(113.55)(in English).-A new sttmosped-ific
reaction was found in the acid-catalyzed cyclization of N-
thiobenzuyl derivs. of epitneric I,22-arnino a1cs. Th~ threo-
epitners give exclusively lrans-2-oxazoliae5, tile erythro-
tep.liters yield otily 20--10170 cis-2-onazolines whereas the,
inain reaction Products are buns-2-thiazolines. The start- I
ing RCIl(OH)ClI(NlI-)R' (1) %vere prejxI. according to the
literature. Physical consts. are given (or: R -R'=Atc,
thresi, tit. 18-19', n" 1.445A; crythro. m. 42-3*; R-Ph
W=CO.-Ft, 1hreo, In. 81-2'; erythro,in.8-l'; R=R'-I"h:
flireo, in. 126-8'; erythro, tit. 103*. Hydrogenating 7 S.
erythro-corupd. R-NIc. R'-Ph ist 99% EtOH (210
till,) contg. 0.2'~_,', ethanolic HCI. over 0.7 g. PtOj at W.
extg. tlt~ alkalized tuixt. xvith ether. and treating Ole
Amsv xvidt cccess HCI in JitOll gave 3.1 g. UICI (R -
Me, It' m. ISI)ANJI'. Tilt! thitiLmizoyl derivs.
of tile amill" ales., lZCfl(OjI)CIfR'1\rflCSPh, %vere prelid.
iT13 %'.:IYS: MIAll"d J.' ().01 limle of the ainitio ale, iti 10 ml.
,C%ll4N ";is li'mud I lir-at. IM, with 0.011 livitc: Plics8cli-t-
tco,ll, tit,! mixt. dild. Nvith 160 till. rt.0, the ether layer
exid. whii 51_~~ IICI, with as.Ltd,s.1n.of NAICO,, theether
tli,t,[. oa, ;,,,,I tile rcsidue stirred with pctr. ttlia and
reco-,td. hIctliod It! .1 SON. If 0.()l ijwlc~ PhSSC_'fl_-CO~,H
'aOtl wa
till. 2N N s addett ti) Oml timl~- tif the antino
:ale. fir its IlClsalt, the mixt, all,,t%ccl tostuld5lirs. at o-,
tile 06-heimiyl deriv. filtered oil and crystd. Nli~thoil C: ,
a 2.P%a4,.1iue dcriv. (0.02 mole) %vai ac!&A to !,,I. of a
allwved to stund 10
day%, dittl with r6), 1. ItLk 't. c
evalld" the residue dWdt; with
Lornfids. of tile getier-d forilitlia,
are givell
I
.%,~,ndrn.pj. Nfe,hfe,,(Wo(la~
petr. ether); life, hit, rr~44?0 (11
:p ther), Pit, Me, Jhreo
7za~
(from CH4-peEr. ether);
67, 13V ([-mat Ciff., IPJiCS,Si
1~ Ph CH(OY)CH3feJVH,,
lfh~ e
jiib, th; Itt'O
m. 141-2*1', iAfi,
32, l1&-10' (filmn EtO1-1);; 34e, PLIi. diythro
132 * Ul'o-11 E(OH); Ph, CC S-t. lh~eil, (NU),
(frain Cj1r, rLietr. e:6cr); Pf , CO.EU, '0;~l
141-41, (f.-o"t F',Oft); J?i:I~
; Ll i, Oren (EXY,
FtOTO !it - V:lCEJ,ju trequirt! 1:1) days fiv
wlsei an iititln. compid, ri~ ~ tit. oxtnililw.
G: 1), in
134-5* (froni RtOfr); cYcloll'ttv], ir)Ara
1-11* (froin ~01/"~ FLOH); -M e, c.-Yelolw-Cy
45~92*(frtitixC4H.-pctr.ethiii-). Clieliz;tion3fla-mvias
carried (jut as foficos; G.GW;nlrole 1WXJ[j:
ad. 1V70 IICI tit EL011 iti a; Wated tiibt~
yellow color disappejjjc~j.! Two thitil-4
distd.nif:tti5niin.,~iiidtlci:cuiiduc~ii
Ittfith'111. V, V11, JK, und V1, uyst. I?CK'OIjZJC!llVNl1jCI
CXITU) deposited, the mcther'liquors Oinij.
ing tiliazoilint.Z were alkahl~id with itq::
petir..etNr, ubc peir, edliT;jtvapd- ii~11141
a2uhlic di'tel. Pre-i the pit, hty-t-'aftcr
thiaziMines with ptir. cthO, sma& irnds.
CliR~NIIBzcrystd.osistari(lipg. Tran4o=atifin
deriv.,t to X111 (comitid., tiri. ilf renction,
XW)*. 111; 2, 62, I9S--2DJ-(J`rom HtOfl-ff,O);
% . . I
and a-ystd.; The
)H)CHRINHCSPh
of. prepn., yield in,
60-1 ' (from CjUr
4, 85* (from Call
e, erylkra (IV),~ A,
U.Salf of crylAro.
Pit, Ifirta (V),~ C,
(VI), .4, 30,
A. 46, SO,-W*
[ATO (VE11), A, 01,
C, tj!i. 158. (fri.
oolnfd~~tiori, ath . er-7
a6d the pmAuct
(XI), A. 17,
1. Crylbro (XII , "I,
WaSS N-3tUll 'Alith 5
tit. I(JU* ulittil tjte
of tile EtOlf'Was
treat i-tl with R t.'Q.
the conesporld-
Ntb, Cull. with:
the r"!1idual thi-
the cxtn. of lilt,
of RCII(Ofl)-
of the lbrleo'
Oield I %, in *t). nf'
n
back 141
. I I I . I
Vr
to

41
SIC

Anigration gave Iltrec,-I'ItC[1(011)CHIfeN-I[B.-. in. W1
11. Relic 0
V: 2, .57, NO-lo (from 5~~ IICI), back ncyl migration gave
_ of V-acyl dprivatives; of I 2-amia Allials in solution., 0
1hren-J[eC11(O11)C1IPhN1113:, tit. 147*
(frorn EtOll)-. Jill SiOer and L%E,oslav SvONXI'L. 13-10
VIL 2, 4 1. 190-l' (from I ICI); IX! 2, 7~3, 2tO* (from
,E1tQ1I-lf2O); I gave (XIV) 1--itglish).-The epinieric Ifirril-: rind cry4ie4ZCJf(SAc)-!
_j CIIR'NtICOR' (b behave diff4r4ilt.]Y it' 461,lic 1110ditItil-
sait, I hr., In. I33--J* (from EtOll-Et.,O). The
coin .-it inWm6li;xlc, it .2-
Iliftrr the formation (if the.
cyclitationof therrythrarlerivs.gave R&l.CllW.N:ClIh.S hydroxvt1li-110illine Fluriv., thr tx4.lu-

-2
ra it % -thiazohii~ (W) whowl file rrj
ivel). 'Icy Z o1$
j(XIVa) (collip'l., tillie of flealing. Yield in 1;~ 1I.p, of x1va, -
,
ii
1
or tile
at
i
if
62
b
1
15
8
1
f
) jpIttlefs give, in oddii. it) cil-2-011:1701ili,; (itub), itcli-
iv
f I
d
RIVNIf
lCl
111)
OR
.p.
e%
,5-
cr
:
,
% 1.
3
p
.
Is
rom
,
( q. o
e'r
,
(SC
T
O
(
q
1NIvOll); IV, 5, 67, 161!-P, ],it* (front FtOll); V11,
1 hilly hir,,cr anits. qF"I thall Of! M di:rivs.
give Stifislatit
3, N), b, 1:15-40", 1.41' (froin Meoll); ill addo., 'it" of 'rile ditlettilit lwfiavior 19 explailt~tllijis follok It::: thl. fortua-
eri,thre-,IfeCII(Off.-)CIlPhNifiCt, in. 189-90, (from 57, tion of lid frota hi Illit Iterielill..-

IICD, was i~olatvd; VIII, 5. r,5, mA5-7* (frnirl petr. ether) In 312111A since. the intr(KIIIC6011 of Uli d.-mbld hr.Aid (liK-q ni;1

75'. -; X. 2, 78, tit. 03' (froui petr. ether),

-1 tile threa-
jj~ueijce tile mutual distance c4 Ik:alld ;;t
i
X1, 1. 63. 1)- 125-30", 147-S' (from MeOlf), x1l, 1, ~w
.
. epimfs. oil the other hand. !ri, ci-t-2-lit IlroRythiazilline.
IN, 130', Ill. PM* (from Meoll); McCII(O
I
I)CHMeNlIt fanned from tile erythro-ephnenj, [be illtl~ilukotl of tile
::tii,l BzCl gavc er;,!kro-.,I[eCII(OII)Cllif,.,NllBz (XV), tit, tjoublu band restilts in increasi-W ~Jhv steri~ hiferaction of
'
I

122". Trcatinr I g. XV at 0' with 3 mi. SOCI:. diqtg. off rhe
4,tht-r-
tt and R, which utre hrought c oser to c',Wli

the SOC12 after!-,tandirig I fir. -it 15', and crystK. the residue it of,
i,tcric r;jctorg will, therefore, Oter4relwitirl ie f9winatio

front Etoll-Et,O gave 0.9.5 g. 110 Sall of XIV, m. ITjA* ain, aftcr Ill. I . ii!t)f!TJA aud l1b,
Ilb, I (It', - Pit) 9
(from EtOfl-RtO); free base XIV, bI5 120'; pictale, in. a conjugation of tile formcd doubl, bond wijh the armilatic
1.18, (from EtOff Treating 7.85 g. XI in 20 mi. CtHo ring. I (R.1 - Ale) do not have ille M"'litility of havine
with a solti. of 2.2 g. NaOll in 20 nil. 11:0 and a soln. of 7.7 such a conjugated *-Stcm 'and tliel ij6re, the; acyl migration'
g. BzCl in 15 nit. CgHs at 15' gave 11.2 g. erythro-
panno UO.'
resailting in Ill will prevail over the folinatiolh)
C411IjC1f(011)CH.,11cM11Jz (XVI), tit. 126' (from C41-1t).. Heating a solti. of threo-PhCjI(SAc)Cli?4cNf1ffz (460 mg.f,
Treating at 5' 11.2 g. X-VI with 30 in]. SOC12, lettitig the sotri. in LtOH satd. with lICI 8 hrs.:at lot)* iIIi;t:tciltlcd tube,,
stand 3 firs. at 15*, distg. off at. 15 mm. tile SQCI:, treating evapg. diesoln. todrytiess, dilg-WjL!3,H,OX~tj. Witi, RtAl
t ,

the residue with 50 nil. 11.0, neutralizing thesein. with 20% f the,
ifter th
and chromatographing tile residue" q,evapin. it
NaOff, eXtg. UIC IML7.111itIC deriv- with Et2O, and distg.. I-*t,Ogve32Om1.(bcnzcne fraction) of Iran j-::Ph:CII'. CI[Afc.-'
.0w.eXt: 'yiehivri 8.9 g- trijpys-Cslfl,Cll.Clfife.N:C'PA.0,

N: CPh.S; pirrale, in. 141-2' (from EtOfl). Feating a
soln. of 3.13 g. eryihro-PliCH(SAc)CHMeN-IIBz inEtOH-
(10 ml.) contg- 11C1 8 firs. at 100', filtering off 180 nig. or!
crythro-Pf;CH(SBz)CII,IfeiVff:.IICY, In. 1q0--2' (from
FILOR-EtM, evaPK- the. mother liquorn W dryne-,S, dilli,
tile residue with HzO, extg. the soln. with 24,0, and
tire ext. gave 1.35 g.
bl., 1,15"; picrale, ill, 123--l' (frorn Etoll), 1'ea-ting 1-98
g. I fit. at 1"W" with W nil,
'-EtOll sjtfl. with 110, d; ifg. i,ff ilit: FtOll, uddiuj; 20 in!.
(130, exty. the mixt, wi;h EA'01. t'-Japg. Solvem, Still
chromatographing thC ICM(ttle YZLVe 1S; F. Ci(lde UTA J.-H
st. Ira n s-2,4,5-tripb enyl-2-th inzolne (.Mif), sit, 93--
,4 giving isomorphouscrystals, m. 68-9', livatingll.6g.
eryjhroi-PhCII(SAc)CJJPhNlIBz with 200 mi, MOII iwd.
~with JICI f; firs. on file slealli-bath, disg. oa tile FtMl.
!.Uddilig 50 till. 11,0and 1") Itil. F-*'O,~Ilterjng Off 1~ 11 =1-YS-1a!S
'(1.68 g.) of eryi~rL-PhCH(SZ~.-)CHPAIVII,.HC7, in. 2211"
Yrt,uq~ EtOll-Et.,O), extg. the mother liquor with Et.~O'
evap 9-- tile' H't--O, and chrom-Mographtrig the residue gave
fi.'219 g. t:rude arld 5 g. Cryst. C;~" isonier fif (TIM0, it.. 84-51.
Ifeating 3.3 g, fhretl-PhCH(SAu)CH(Ct~.~~ t)'4118z with
100 till. 1--toll Saul. with MI .6 !
.IrS. rr ,. thc stva-m-bah,
kfi~itg- all the EtOH, cli1g. the resfolut -~-: 4
tim. soln. with -h ,-120, arri. extg.
Et'O 9ZLVe 2.9 g. of an oil ;"Ili;vlk y;--;'ded On
I builing "~itll Pert. ethe. 1W g. in--vil. Iran ,
rcarboxy-2-thiazu1ilm, ou. 13T-8' (from C. 'I
1.02 9-1
1105-6' (from'par.'eilivr). Similar treatment rf l.(~5
gave J50 Wg. cj~~
is M 11.
0
1,arldlY(fromrnother

p
-Tiquors,a(ter ti~t-tlent oher).! I.Yeating 19 lifir
gave IV enchssiveiy. IV wavoili6itzed 61 6&tixir g I hr~
0.52 g. tkrea-PhCH(SII)CH(NHXGEti iiiiih 0.3 g. Me
~1
~ -0
1
(OEt): NH in 5 irl. CIICI,, dild- the. mixt;: ivith -10 ist
-'IrttO and extg. 3 times with ~a ~:5mall vial. 19-0. kleatiliff 1
'910 trig. nil. E 01-f
-satol. viith HCI 4 his. ou tNe'fiteain-traJ:.h;jr.We 510 Lug;
( VI), bo,s 132'.
Simihir tTeatmvitt of gave:
1-1.51A, cis iso)t tier of V1, in. 07 ~-W, ( froin ii~i If. t I her). 111fra-

Cot kirldilit UXAZOIWO
rroj 51J.'Lfra Of IV and jj ;Xnd 4), fit,.
are giveii. 111. Steric toune 0 the r~attioll of N-acyl
of 1,2-aminrf 41COW& wltt~ 011011~t C1110lidd.
jiH Sick-T and Al. ildhIc"'I On LUOV4' :'Cilrlu. 1.i3fy 40
l
s
It-
141Y
20

.
-'50
at
Cn-
,
2"Ji
N4 ~D.55)(in Jtlciihols react with
'
eirlivr 2-oxaw-
50cit ac"ding to tile to *glvd~
line (with inver~;ioij), or z. e-ch.kro amlile (witbout inver-
min)-
gave, after it short action 6t SOCI,
;nt!tlil,l-r~-I)heliyl-2-oxazoline (11) and on Pffitonged actions of
SOCIj by a 5econtlary reaefilm

NO (IV) yveld&! by the roOkii wilb %)C1, 30~r, Ayev-1
-
' f
lydroly-~
P E ICICHHoN.11 C.1
1,MOLj~ (TV) a rid prOxi bly ill, I
, 4
bis (if which pive 30%
NH-.HC1 (VI). Ill and V weire rot foimi:d by sixondary'

"v 2-otribAlues since tbc
dralysis of thc C'j
are stable sinder ike Con1fiii(li ai'd rc~r the reaction with:
9.301. ifireet mixt. aftcr!
the qCtital of SOCI. ;Ipon W~ylelded. is tiii:it, of erv!,
l

11,; wid'i
t ratio (if 11ired to er-4hrc' =i'
and th"a-amillo Vd.-ollf t I L'
3: 2. Tho~ qvo.~pfltlwiag. coirplj;s erythr4- ;1'ad lllre~-AICCH4

(0lI)CHPhNIfC0CII,-N0-P (VT1, V11f), and in-fkro-
and ax. K)
were fran,fi-irriied, %Vitli jurVersion, to frarix- and C; -q
'rant- and
:!-0XiL0lli1lC (XIII, XIV), 'I lie diiii-iLint t-,.uit ,r flif- rexAl'oll I
4,f SOC12 with IV is a"Cribed to (lie pol-
ar JlL~ t (d the I'll'
c
group ~lllcu rise corresponding cyclo~exyl deriv. X behavc&
U-n-nially. Ilydrolysis of tit(: d-chloro arnides afforded the,
correspo" ding derivs. RCII(O.CC,11,N(:)2-P)Ctllk'NHUliCti
Theantincialcollolswerei
prelid. front dw appropriate isonitroso ketonei by hydro-
pvnatimt over Rancy Ni, or by the Mcerwein-Poruiderf rL--
duction of P-nilrobviminfido ketones during which form;'-!
tion ofa 2-oxazolinederiv. was observed. Thethreo-clilimersi
ivere olitaiia-d front the rr 'wAro-epimers by the reaction with I
SoC12 Hhavi:rl hv It.% drolyci~. The cvclolicxyl derivs. were I
.prepd. timn the I'll detiv. by hydrogenation liver Pto'.'
,,iihr,,-I'IiCII(Nit~'iC[[iNte0lI was tran4orrned to trans-0-1.
Muth 'v1stymne "Xide (XIVa) (infrared Spectra of cis and fratis
qu,xiflvs are given). The 2-oxazolines of cis and trans
C'.11figuratinn were prupd. for identification purposes frotu
vtltcr~ amf the amino alcohols. Hydro-
rumition 'of -107 g. tij.Cme: NOTI in 7.5 L HIM[ over 160 g.
R:nwy Ni at romn limit. and l2iYiO atni. gave 150 g.
(XV). in. 101-:55'. RVflLiXillg
It .2!;. I3zCflMeNiI..IfCI with 12 g. p-0,NC,H.C0CI (XVI)
in 1.50 tul. PhNle 6 lirs., distr. off the FhNle, and rrvIt 9-
(lie ru~idne front FiOlf gave I I q. 1J:C1L1!eN11C0Cf.114_
v 123--l'. Treating 37 g. IIC1 salt 4 XV
(XVII). in.
in :300 nd. 11~0 with It; g. NaOff in 2(.10 ml. lfzO art,[ 33 g.
XVI in 500 in[. C.14;50 lain. gave 55 g. crude and 50 g. pure,
1. tit. IISI.11-90* (from EMT[). Tlic sanie compd. was ptclid.
hr rufInxint, 2.5 l,r,. 9 g. XVII vith 11.2 g- (i--Pr0i-Al -%nd
2fm) fill. i--Pl Off. l" I,e rv~iduQ ift-.r th, t-apn;
of (lie -s"I'ent %%ith Ini. HO, 1w evat'g- l1w Illixt. :,ad

extz~ the residue with AcOllt; hi a 3,ielcl 415: g. DLqsolvm'g;
4.5 g, 1: in 15 ml. S.00a, tvupg. the .44n .:, 01-isralving the
r6idric in N)'~, 140H in t1w pfv-~encm t,4 8:rni.. rVV HCI irl
the 'lA). 5-Irlt di I'll 1, it-ill) C
l
;131111., it 11
1
14

1
F111
by alk i. T
l
gave onfolAills; I K. Ift"I ).art bf IV, 171, t'.1
.. I
lb-'ation Ill a 5 1
,1d)
r holiC M)~ L1011). R0,
!!. 170"
~
-to beg., t-xtg. thi: soln.
,)
;
fluxing 1.5 g. IV V: It 1 /6 ITC1
with EtA evapg. the aq. wbi. III> dryneco, krid crystg. front
Et0fI and EtlO gave 0.7 g.'ik4r,)-l'ACLI(OII)Cll,ljreNII,
H0, ill. free base (in,06-7% yleld front the
,alt in Rt,0 with dry N113), ni.*71' (fr--.xii Cill1l). Hydrc-
Miation of PhC(: NOII)Ac ovtrjLanev Ni km-e 531,1,, ervIhrLL
V6aing 2~.2 c.
PhCIlAcNH,.IICI with 2.4 g.;XVI ill:, 0 MI. PhNfe 4-5
firs. gave 2.8 g. Ph CHA OV11CC) C',jrlVorl (XLX),m.IW-7*_
,
XVII
1 and XVI gave 807c erflhirc-Ph CH(,~ 11C0C.HiN0,P)-
CHAfrOH (XX), m. 15"'. The saine'c unpd. was prepol.
by the Nlcerwein-lloundorf r(Aimion of KIT in, a yield of

s. isolatti : all a by-product.
of XII, m. 125'. iv`
'
e reacii0t, If XX will, SOCIIintj Lbe sijl)54jquvnt. hydroly-
Th
sis gave 62% of the HC1 satil Of fAre0-PhCj1(N11C0CW4-
Xl~xxl), ra. 2074, ~ free lv~e XXI, U1. 1,514'.
%,O-P) Crime(
11yarolysis of Y.K. gave 55 %~ IA,-t,tt-PhCfi(,vlr,)Czflfcofl,
tit- The rrythro-o-affiglitation btXVI11 V!Is proved j
by turen. PhC1j((711Afe011)XAre.1, ra; 47P (Yield 56")
and by tromformiug it to X Vii. Hydr6gliliation of 10-5
g. of XV.IjCl ill off) 1111. 99, '.17101i -okr I z PtOt ill
the presenve- of (M vil. 911~7,- EcOll salA. ai I),
,
ie~: pvc 8 1g-: crvIll'o-GH11-
pi, nortual preirt
LIPA'11,. I'm (nW. XxIi. and XVI
cill" yj
'
~
i
e
l-
(I'min 7.5"C' Etoff ~
Sijnilarljr iiias preful., by
i'l. i
l
hydrogenating the Ared-PbCl
C411,,C11(01rPC1~,lFeX1Tt (yi hU i4W~,;). ;111-~ (fmil
petr. etbt~r). X;tr,,bcnzo3),1tjoa gave ~Wllv Of a crude
colupd. c-ntg. di-p-nitrobmitoy'l deri1r. 11 V~asl treated

Tlkl
With Ili() l1k:I itt"ViOll
j
wivi thns tran4omic,l to thc IfCJ i,,W11; yit-J&A-~
(YXIfIJ
1,
Ill. ~jmc- Collijill. waq
tit. 120-1' (from EMU). T
prefid. by livittilli, X111 with concd. I ICI by way of its IICI
halt, ill. 2(m) -I' (from F tOl 1-Ft,O). Tilt! reaction 4 tile-
P-11ilrobcazoyl derivs. "r the amino n1cohols wiij carried out
C13 (1-21 till.
by olvilig tile voolpi. in a will. itilit. (if 60
, tile. 11INI.
per 1 g. if OIL: comild.) ill by !Iuatillg
aftvr a "itain little with ice and ACICIFt, by evalig. tile
At:017% ext- and by cry,tg. tht, residot, conte. 10 of the
(Starting avyl deliv., jillie of action of SOCI, (ill min.), the
product, in.p., yield, and the yield of thv comparative
cilo1j)'j. pit-pd. by licating im tile stemii-bath equiinol.~
allits. (if aiid Et p-uitrobeuLimitLtc givenl:
1. 1, 11, 77-s', -.S"I.. 641 VII, 1, XI, 125', 77l';,, 811,-
Vill, ;~O, XII, 121--2-, 53;,~.-, IX, XIII,
W*;,, 751'j,; X, 2 it], XIV, 124 -5'. 721~. Di5solving,
'OCI
1.5 g. IV ill 3 oil, ',i --, dcomipg. the mixt, after I min.
"1111 ive, vNig. with e'll' rave V, IT-fi, (frVIU C4114).
I VI, m. 9-15' (from
T iv toot1wr liquors c,aiuitwd :if)'
fit :111,411tr e";.(" tile rv,ilftle the vV111111. of
C,I 1, from t he :x
a. (2.,~.! g.) va, -Ilux-[ 6 hr,. witit SO till.
soill 2 till. :!~N, I JCJ, tlie suio, ev.111d, to dj-~ jjt!~S. Elie rcnidite
vxtil. wi0i hot C.,114 pve 0.2 g. and threti-miii(Its,
'Mil midi~~ofv,d :~-QS g. of 0- M-,- -ld ekytilifo-PhOb
llhich w:lu traltsff-rilml by
W~A llli~',IA(ilill Ili 1-1~1 g. 1. 111. ISO '41' ~Jnwi P(Off)"awt
(1.7 1 g. VL j1-~,Vjj,jjCj,
M, 210', %vit, ihti,ill(d ill a W, vivid by If-Itilig I mill.
vi~ i"mi'r (Xxlvj if 11 s6rh SOO., d'O'llipi. ill,' lllixt~
kith i~-v if:,[ vmg. kmh A'OFt; s~fl 4 XXIV V3, recov-
T'L tit. I 111 1". Trai"folillafil.1L of tit(. -`-ox~, olit ws ill I-
11"roacyl 't- b% dry IICI into a
V-ded di-i,ioc sn,pcn,vill of the o%~tti4iilv, by. Imiting the

IIIIIII all lit Ow jfeji~jiu 11j;H10it, hytv,Oj
. III I ~
: i; did
~
jll
110
"
1
10.
7

.fit Itiffil, and by IlvalliIii dir mijilkirio"il-ri mil" At IM-431) .
(ril-I!Ould 11), or fly wiitl~ prif,"! oF6.)Xjnt
(metho,j C). Thti~~ lollowijig B-cllll*oac~-Ij
aloidci, riletholl'of prep'j", yield ia In.p. (iro"I C#ff
'
1

"
Cj1j,Co-.C1Il1CHI
dand III P;O,,N
and It, It', % yiel p. [if
NII,.flCI obtailit"d by pelli"xing thf!~ dilarucyl WilidC.' 1;5 brii"
1
'u, 13'
oil Ibc ~qvaxll-bjth in W, A, 1, -1;3~, lill'i 4:~~
,
Me, flwe(i, !);'1, 210'; V' Ii b7, Ph hic, Crythio, 28,~'
2 12
156-71", llvle, Plit, threo,:62, 198!'-, jhreo-3fcCI10C11ph-;
1
MICOCill.NO~-p, B. 49.- AN, Pli, erythio. 33,
202"; 3K
140', ble, I'Ardit, 55, WWI; 111-0- CoUttC110-i
C11JreNJ1COClH,SO -It; C, 7,jl,'~;' t40-0; mcbver,4
100%, after the hydrolVi;ls, vvitli 7W;e Rtoll. iv.,
action of 2-ox-azolines;luith tblda6alia icid, Neiii. syrt-~
-' I.
theses of irc-aniino t1ii Miroilay Sv~,ob~w a, jifi fReher'
44 .

1.
,r,
jm Farka~, alld --c-tem. I.` .
till Wy 49" :
Pj OF VIP 426-

FIT vmw. 20~ 1
H el".
&if ilie kiiiii.,rid
Acff Id tive
IbCII(SAc)CMt'.NLICdi4. Thi. it-actiull is nut Io-lkeral
hilif Nvith certain di-rivt;. UIC -1-maxotilles havill-Olt
in position 5 show difr~t~nt m. livily fo~ the tr:LiIS'
isomers, the latter lidnij uitlch.l,~ss rem-ti%(t. Cis--1-1IheTiyl-
(Ii ,lot)
'
I
gitvC ni. it,
rlnal neth
1~
%v fill, (mliolilles tii;vt!d from ci~- auit rmlri-.
itil.
Uld
e-:!-Oxll~ohnes -actt-A Avidl AcS11 dill"AcklY atidy'
:
gave
1lvxa7,4t (V, VI) %vbj6I1iVQfU Jr1jlj~fL,rIlIl:d by lilujus (if IWO11

7) R S
(VII, VIII) 617 rlin~d'v-
to.cis-pul' trans-bcnzoYl 111,11og,
,1he cis deriv. III ga','e tile ut ~`rtnal product
qX) it, a(14111. to Vj!
y dillerent (listortiou-
.The different bf,11,tvior i-. clplaincli I with
115 b:
cy('jiC c(flifonnatio,
'of tile Mutual
rjjj~ atiliclatioll makes
tile 5-membercd oxazoline, ri,11.9-,, in ju, ea,,c of IV. Tile
th, C-0 bon 'I .01flost inaccessib
liols which could not be prepd. by tile abode
diacylattlino t1 by the reaction
proc'edure from tile oxazolines were prepd.
Duritig tile prepri. of
of Af:911 Nvith tetl b:
tit(! reaction with fit,
oxazolines from he o"ther'
the threo epiniers showed uluch
benzimidate, ', zolines
reaction cour! jilaij the erythro deriVS. The 2--o%a
were prepd. as -Ikoxs: 0.m 11101C of tjC amino ;klcollol IV"
fe oil
ate 4-8 hr4-
refluxed with 0-i'll I 11joh, of Et benzimid
tit (ill roilw CaWA 1-9 firs. at 120-41W), the
ille wil';
1701(
~d u,d,tf! Nv,t"
!'phy diAll. (M thm
crystd. to f-hroinat0w.
or sit
was addctl to
A). crythro-l[,I~Cii(oll)clllll%Nltl, (.1.35 g.)
llixt. to stand W
11, tile I
.SO, (20 nil
con d.
ith ice, tile ujixt. neutral-
inin. at room teinp., mixed
r' NaOll and tit product extd. with EtA
ized with :30
-and CsHs to ~j' ,, 3.02 ;~ of the traits-oxazGlille (rilethod M-4
The soln. of 1) 01 itiole amino in 10 nII- ClIC13 "' ,
61 moic 'i%IeC(OEt): NIMICI ill 10 "d- CHU,
mixed with 0.
o 1tile, %team-b.01; 40 lilt
the mixt. was licated, 30 nlin-no~.c
F,t,O was ad'&d the NH'iCl rel d, and the solo. ev,,ipd.
following
to dryness Thus were prepd. Ulf
Method of prepn.,
RCH.CITR N.~COR'I-OC)(X), (R, R', R',
L
Yields in and rri.ps. &jjj)- 87.6, bg
.151; ci:-ph; fill 1h, X. vi,
. , I &3-4~ huff ~ im-3
(dilnorphuu.;) (frelli petr. ether): JttjjJ;~Ph Ph, B, ~3,5
81-5' (front Petr. et' ~r), 93-4* (fr6triNfeOlf) , : I
fillmor-phous):
Cis-11111 CO-Et, 101- C, 67. 11..;1VIA11 nyli_ ~1
NI
e. C, 81, Ill 109-it*; cis-P.O.'Nall, C1
0410, m C,-7,'J:
14,12, (froill Ftolf),
.89-W (ftom cyclohexalle); lluliA f CO:41, srp, C, 67.
111, Pit; ~ A e, 11, 59,
1 Al 94,;
[~.o 8 (from
lihroitle); 'fe, cis-Nle,
3 Ph~ jfi,~Ql, Ill
Ph, Pit. A, 00, bf,-a 14V. The
zolill (0.01 rpole)
was dissoNeci in 2-1 in]. AcSIT, tlje~ ti)JIL aslio.ted on tile,
W
steam bath for tile tinle given, the: ACSH as evap'd. I .n
MCUUT C6110'ea5ladded and againtviijid. lltik' atid R 'in X
tiMe Oll lirs.) arill temp, of heatiiig;~ylelrl in and
I;p
or RCH(SA0CfIR'NJICOR' are gWzj1j: ci~ If
5, 100% 75%. 133-5- (fst),11 i!-.o_prO
Me,
Pit, 4, 100', 72(,'r, 129-9.5' (firoul i!to~,Jft
"ge, OR), irat, 2-1 hr3.'
tit .4
-pit, 11h, Ph ,
5,21, Yrouli
Xr
iso-11troll or Colf.), 'Farts- too!r,
ph~ 11121~ ii'2, 225
(from C4114). same, 12 lim, ~Yrl, '7 ;%~
C011
Ph. 4. 100', 72%, Q&-$1 (from is~, 4,011);
COSH, C11
2, 100*1 PhCl1(S( 12 CII(COJEL)C
'OCIIC, NlfCOj'jj;.
trans-ph, COtEt, Me, 0-5, I(Xi-, .92 ;c., 97-CV: (fruin C,11,-
pur. ether); frans-P-NO-Csr-14, C0114, MC,
Ii, 100" 731/0,1~
.139-40* (frota C'utt-petr. ether); ;rejs-ph,:J`h, Ale, 4,;
i 100", 4 167-8,; Ph, 1i : low ~.5,
eis-C,Hn, Ali
1?5* (front PeLr, ether); cis-Ile, PI h, 5,: I(jo*, 54%.j
P
:12G-7 (from i_r;o-Pr0.T1). Muxin 0 L'. I: with 0 rni.,
j j:

AcSlI I br. on the steatit b. c 7.9 g. 11, tit. 13G-7'
ath g3v
MOCH.PhNi'Mr. NO---!". V,,: Syntht
lis and configursi I
r- Coll$). Refluxing
(f om
-
01l 6 h
t
l
E
it
h 3
l
hi
l
i
50
1
32
tiOn Of Wit Tacenlic A-PhellyleYsttines. ' 'fiii, Sichtr'
- S
~l
b
d
:
.
m
is, w
-
anet
o
ll
t
g.
cyc
open
,
g.)
(
,,
vo
av
63-74
a,. and j if i Fark.A. ~ Chens. 1
0:1 49, 1:
,kl(iso,_Pr0)z, treating the mixt. with 200 ml. Z`a twtaric' C.1kaien. chem. C0-4-nun;. 213,
acid, and extg. the product with AcOEL gave 0.77 Z. hans- -(in EnglNh).-Camrary to AcS.11, (21-10~0-61-1 adds tut.
iV-ben--oyl-Z-c"iint;cyclopentaneilzi6l, tit. HeAting PhClf:C'CQEt)~NHBz (1) and:",NQjj,CIJ: C(COEj)~
9.6 g. IV with 9.6 ml. AcSH 2 firs. on tile stearn-bath vielded (11) and gives lbre,~-PIACIf(SCOCIICII)cfl(CO-Et)~~.
8.85 g. VI, tit. 159-,60*. Heating 1.5 g. VI in a mixt. of, NHBz (111) anti. threo-p-OtLVC49,ctr(scoc~i'-~l,)Cll(CO~~
dioxane und water 1:1 with 4.5 g. Ag-0, 1.5 his. on the D)SHB.-, (IV), resp. llydzolysis.of III givd Ihireo-PAXII-'
steam-bath, filtering the mixt., and evapg. the filtrate gave! (S11)C1f(C03FJ)NHB- (Y). the anetylatioll of'Which yieldedl
VUI, m. 120-l' (from ligroine). Healing 8.0.3 g. III with lbreo-PliCH(Stc)Cfl((-*aEj)lvlln.I (V[)- A6dic hydroly~ i
9 in], AcS11 2 firs. on the steam-bath, di5tg. off the AcSif, sis of V'and its rythri,-upim
I e1, erylbr
lidding pctr. ether, and boiling tile product with 133%0 gave. .(COFt)NRBz (VII) (see part If, above &Ivc tra
ns-2,V I
Sol. V, yellow needles, tit. 1:39--40' (from Cilia-petr. ether), diphemyl-4-c4yboiy-2-ihia:,,ol:nc :(VIII) at I :IfCl salt f~
and 1.73 g. Sol. trc.,r;s-~N'~bcp-zoyi-S-acetyl-2--dniinocyclohe-rane- lle:* Same result.
thial, tn. 146' (from iso-PrOll), Irans-jV-AcetyI-_"-amfna- -was obtained by the hydrolyjis (it ets- anti i~uPis-e.,hyl ejj~j'.
cyclohe-Tanol (XI). m. 124-5' (from AcC)Et), was prepd. (X,X1)ofNM. V111 Nvas also obnabned frmn
by p.,u9shig 10 min. CJT`2:C0 into a soln. of 1.15 g. Irons-?- Nil and TIC) Salts of IX ur;4 eryIhrJ-PhCl1(SH1C1,f-
allullocyclohexanol in 30 ml. 11:0, by allowitig the mixt. tov (C0,10NIT, ()(11). The action'.4 HC1 iii.,EtOll traim-'
4tand 3 firs., by cvapg. the mixt., and cryst.,. the residne
1
,1
V~
f
1
A
OEt
M
d B
C1
b
1
2
0 formed er3lhtt~-PhCH(SAc)CIT(COtFt)'.~rtiAt (XIII) to,
'
-
C'
PACII
SH
Vlr
h
-
-
-
-
ra?zs-1
rom
ace.
.
an
c
z
e=y
gaye
; ,er3
ro-
~
t
O,El)t
,.IICI (XIV) and to 2-
)CH(
(
aminocycloheranol, m. 190--l' (contrary to the literature), I i'melkyl-4-c~rbelAoxy-5-ph~nyt-2-tls-.'iiaotine (KY). Hydroly-
Adding 1.2 ml. BzC1 in 10 nil. Et~O to a cooled soln. of I g.! 'SiS of XIV, XII.HCl, or XV 6ve MHO., XIII is thus
'
-cyclohexenimine (X11) in 20 ail. Et20 and25 nil. 20~50 NaOU, ~
m convenient mat4iaI for the prujin
I I of:both racernic
-
Bepg. the Etti) layer, and evalig. the solvent. gave 1.5 g. I.plien3.lcystc~et~-S'IX~2n4;Xll. Hi"ng 13;3
'g. 2-phenyl_~
.,Y-bct:zoi,!t:ycialiei:eritni~te (XIII), m. 77-S' (from Cillvpctr. 5-p-niu-oteiiz5-lidenct)xaz,)Iidoni,, bi 100 nil I P-joll tind 5 tnl-
!ether). Mixing 0.3 g. XHI with 0.6 nil coned. H;IQ, 2 firs. 013 the, ittaiii-hath gave 12.3 9-
0.34 g. Iran s- N-ben 2o),I-S~icelyl- !-a tit 11, m. 165-61t. Heating a mixt.~;of cliclic0sli (25 mi.y
I'll-51 (front C,116-pctr. ether). Tre~itjng a -Aii. of I g. -pith 3-1 -i 1 6 his. on the steani-lath, adding Et.0 aftef
XII in :3 ml. Cilij with '1A till. AcS11 ill ~3 ml, C,116 andi 'Cocling, alld crystg. tile White cry'Lll!; fr~AIIIUEOJI &a-;e 2-1.5
eval)K. tile sulvcllt icave 0.3 g.
hi-ximelhia!, tit. 120-2' (from aq. FtOll), 11ca ting a S'A;1. of Roluxing 2~2 g. TH with I g. !i5Ai~Pj0il1:i1j "'t) rld. I"[011,
1.8 g. 63-2,3-d if llwnyle t I I y lell iln ille ill 3 mL ACS11 A hj-s,' '4 firs ci-alig. tile suln. rViidue with
'
on tile stcarn-bath, EhStif. tile excesi AcSll iti t-t;,:ja, arld 15L'." tartaric acid, and mtg
'
, the isyst. prodli~t With RW
Srystg. the residue fr,lm aq. EtUll gaye 0.9 g. Arev-PhUM gave 1.2 g. V, m. 126-,U' (Fr * ..
#s L"'t )Jj_*. Similarly-
)~Fxi. it . ; I
0 V

To? I
17-119", quantitatively. V and Ae,.O in pvridim- gavo
Ill. 12G-8, (frwn b"o-PrOll).
Heating L-55 g. X (for the prepn- rict-, part 11) with 20 "it.,
Etoil Satd. With 1ICI 20 11173. Oil the '3tt_-.lIII-b4tlI, eV:Lpg.
the soln. to dryness, dissolving tile residw!' in ff;O, and
extg. with 1-.t,0 gave 1.23 g. of ill- (,if which was :sepd, by
extri. with petr. ether into hisol. Vill, In. 137-8' (r,oin
Cal 14), and 350 mg. nx,). XI, in. 05-0 (frotri petr. ether),
;Treating 620 mg. X (or XI) in I lilt. rtOll witf, MAJ flit.-
Nuoll ill ~" lilt. rtoll, acidifying tile, solil. with fICI and
extg. with Rt,0 gave 521) ing. Vill, crroneously forululatvd
as PhCIf:C(C0.,lI)NC-AIh by Lurje and Gacenko (C.A. 47.,
-- - -------
216,8c); Na salt of VIII, In. -962', obtained by NaOH in
"F?'[[ froin X and
J XI; picrale of V111, in. 165-7' (from iso-
PrOll); 11C1 sall of Vill, in. 1U-7' (front isci-PrOH-M,0).
Adding PitC(OEt):Nll (0.:13 g.) toa soln. of 0.47 g. HCI salt
of IX under N, dilg. thc~inixt. after 24 firs. %vidi 11,0, evapg.
In
racuo, dissolving the residue in Et!O-C.114 ruixt. 1:1,
Washing the soln. with HCI, evapg. the solo., and crystg
tlie residue froin Call, gave '1111. ThesarneCovilid.W1114ob-
tained froul XII. Healing 1.65 g. V with 35 in]. 15
10% lie
-lirti. oil the steani-bath and extg. the mixt. with EtiO gave
0~35 9. Vill, and from the aq. layer 0.17 g. IX.F.ICI, in, 198-
9' (from EtOlf-petr. ether). Similarly VIT%gave 3S,70 VI
and IX.liCl. Heating 28.33 g. VlIr 10 firs. on the steanl-
b,ith with 70.9 mi. 10'10' 110 gave 0.5 g. VJ11.HCl.by etiler
cxtn. RzOff (6.9 g.), 2.1 g. recovered VU1, oii,i 1,1, evapa.
"f the arl. lay- 7.1 g. of MUCI, in. was
transforined by esterification and herizO5,1:16"a to 111rea-
PhC11(SBz)C11(C0,Et).V1JB_-, Ill. 181'. If a ing a sits-
pensiun of 13.25 g. Alelf: C.CO.S.Cph: N ill ~201i) lilt. EtOlf

--
. .
.. . --
. ....
.
-
-
-pg. the SiAn.
5atd. with If .1 firs. oil tlt~ Iteaul-Ruttill, evit
to diryllf--la in rcclw' 'Idding1lia, cx1j.'. flit: inixt. Wi6:13t,0.
je witil Oar.
le eat, to drylleM,; 1 -91
evapg~ if wd extgi (lit ri
93-4 Ind
: stil
X
m
3
6
Vill
0
.
.
.
1111g.
g,
,
,
tther gave 40
'
gAILI Irith '100 in]. rtoll 6itd.
3,7 g. XL Refluxing -in
with FICI) 10 hr%lya the s,,v=-batt E-',Lve VIA 9. KIV ill-
7
loother liq ibri
(frotot iw-l r0fl-lit-k), and f1plii tilt.
q
Heating
by I!Xtll. with E
It. XIV Nvith 35 lilt. 10~~'t, IK! 4 firs. eii Ou stcarn-bath j ave
4.0,1 g. of tilt-' XUAWI , go,-100":solidifying and, Ill.
ogain at 1`78-13V (fl`011111 1( 19-1-51 (60111 ko-I'llOH-p4tr-i
'
tillg i).i;. i;s; X
-
ether). Hfa ol;j lie] 5 tirs. an
V wjith 14 l
-')~ (froin EtOkf'
the stearri-b", h gave 1 g. aj[Cl, Y i; 104
t
)0 and 60
Et20)- Sitailarhyi, _i~ (if 1.65 g. XILI yielded
ing, of tilt: Hel salt'i of ]EX,und 'a[, jej'j), Heating 1.66 g.
o inin. Oil tile steam-badi oittler
X111 with 20 lilt. N NaClEf :1
N, acidifying the soln. witYA JICI IVL pll 2, and crystg.~*Iut
Ph CIASH) C11-
1h
i
ro-
er-Y.,Itals front If,() grj,,t ().(
s g, Ary
c, m. 169'.; Reitting 1J.5i 9. Yj1l with'l-~I 9.
ILI
C 11
1
V
)
(0
-
in 20 ml. HiO 10:hrs., rernovinjr. Bit with
(6H
2
)
a Ided Sri): nif. 1hre~0-PhCJJWJ)-
and ev pg. tile filtiate yi~
C11( C02jj)jVjjlc, ra. 146". (front 11.0). 'Esterificatiou of
tile jjCI salts of IX arid X113vitil tict Ill Lit Ilbyrt:fltixiilgl
1, In. 148~9*
and'd firs., resti., gave 43c threa-eplolixof )at
,
and MlICVwas
(from EtOll-petr. ettu'r),
esttxified and acetylated jib Ac,f) In. pyridine to give
v
105.5* (from, C,H*-
thre~P1,C]I(SA0 cjf(co'l
petr, etil -rient of;XIV &vt!
cirl. Simiilli~f
-in
eo- and lrybr-PWCIASBz~01-
rt)NHBz uIld XIV 9;lvt';Ilii
Vi-
In. told
figuration of I_phenyl-1,2-pr~~Panedids~: St~ric course of tho
~hydrolysjs of c; - and lr,-,rs-l.ghenyl-~-rtiethvletliylene olide.
'
'
da wid filli Litry 49,
Sbob
o

iPo'
W1.
English).-The r~,a -on ~S-. an- fYz;*;C-
P,~;-ph h all r a'71 A" Y161
f-i7c-A of , ",V~ - , htid IV
PhCII: CHIMe (31
'de Q- Rm wl'i 11; Wn
Irij- (111) and frans- ~-X- give-- a mmtt. Uf
epimers a 5, Pri 5 1w-;*-j1jO'5~mI
nd are no-, co'-'fT~y .Fj t~3'!
an.! ~7
call'y I wnogt
eye
ps, tlig. thiv
a I~L'witfi prviui!ing vyls
-iixt. wita C~, i -, acd thie ;rziljd~Je' g'Lm UPO M&I.,
b1n I teld 4 fAr,!"-
(V,)'t,. a ti oruva
p=ro S:n:;Lf wt-t- Gbtair".=_' L-7 ~h-- fiss' "=-`Ctys~ mstduc. IN, ioZ-V, y,6!,h-
j"y
~e'7 ';y ::11 1-1.16" L' 1n-X- WM9, (M'% IT =' C.7% 1f_- th~
.6f III and IV. I to r~
both L~cmers on;tle cjjs~ "i I-)" acid)
12 sc."
fli-ith KM!-.~-% o.- - N
.-v
M
I -"::Tea
. -: 5.9- mint. V. I g- jtjj
4
.-as 'mat at -4G* -W
HCO'H andr T65 Tnf, 38,5%. jftCt, slkri,4 -he MM-.*451:' IgSG, 'Yp~ao I in 350 vx n
ed ML ..2-i the 1,
inin. at 40" allowing. th-, tv stand at muni
the exm-:3 -d HWIf. -.n --cmi, dry- Y;aa~-mt With hot T-itoal aud theM1L#-ft--j
-h P.
jemp., distg. or
H 'due was di,;,-:--
C A "- crYsf. res-, "ved bi a inj i,:a:mt 4' altd.,
Ist
ing Me residue (7.7 g.) by d' U. IOh Q111'
tit. irifth Etto'. the -A
residue in 60 vJ- Ft~O~ tneat 61-19 - sclia. With E6 -11. an- -yat'j. from Was e?4- -f I es
IT
MAW, per the
ether soln. couM t' K Ing. 4
ur
'alixt. I br. or, lie 3fcam-bath, d t, .9 M, -
HiSOt in 90 nil, HA -"iHl S
vC by
ing the residue aftcr the cxapn. of the g;- 'dH�
1 ion Wit,
ejUtiOrL 1.3 9. of an oil not iur4.1,tr iden6,
.27 g~ 'K, I
-S', and by Etffli L
Et,O 0.25 g. V, ni. 8&
""Ie Ob-ained by hyt,ru"
in. 50 *yz*,
-59P. Similar results
"A I
the intermediate h-alf-formate .v;th- Nal- 1. 1 (bj 31- n,
H rn
~1.5399) (5.9 K.) a::,1 a ruixt. 'A 3i.3 g. 11C02' anc 5.6r, I
'38.57o 1110, gave in tl;t: above inanner a smll armt. of impure
IV and 2.45 g. crud(! VI, !-n. 38 -12'. 111 %vas nbmi:-.c-d from
Ar
"-fun

p
alarographic detenninatipa of rqf of perlqd-t~ 0""
Skh
of epimeric open-cham 2 1 cgl.,.L 1~, i Z.
~~Pmwv ,
M. S,
a, and
;Utc-S orl! -no-a' [if a Scries
of Steseolsonleric flairs of Llycols
periedic-acid- are dutd. poluogra~hically. The specift, -
2ad-order rate conits. (I. molc-- ieQ.-I) for the i,,omctk-
pairs (given In th~ order threty, cryllu,o) in 6 X 10-$Al* KfO,!~ 7
and BXIO-4-11 glycol aq: soln. Lit 25*, hre as. follom- A-'
-2,3-dibl,
PIICW'Ipr6pxne 0." 3.7; ~ butane

4.8; h.8, T4; ociane-4,ri-diol, 5.5, 4,9A
hexane-3,4-diol,
0
,
paxi.
1-~yetrifiex),Ipr6pitiie-1,2-diol, 5.0, 4.6; -1-phcoylpro e~;
1,2-diol, 10.1, CC); . 1..(p-niethtixy~lirayl)prolianti-!,Z;drol~ J
5.2;
11'
let lanc'u)
2-41
hen
6
3
7
(
h
lb
4
241
l
.
o
,
utaue
luet
,
,
;
p
y
,
,
y
:
-
id
d b
h
ff
f
(it
l
as'
ect o
sm
an
.3.
T
e p
diol, 14.2, J
u
IINO,, 11OAc, NaOitc, Nall,V0., and N4:100i) amilhi
rke of reaefloafto the. two pairs iaalru gWen. Tltccffeetii!~
of mol. structure on the ratc crinsts. are dLeu.'sA.
ping

C,),. rt L r ze c h 0-~; ic- G-1
~::~t crr o ry
ba. i D,1.-,
R'll". Zll-m'-.-aLdYb. 19286
Atithor L-12mant I.; 91licher, j.) Krupicka, J., SvcLboda, M.
I n 2 -L I't U 'U.
T t'w- 1. S'tereochemical Studies. VII. Pericdate Oxidation
of Dlastereoiscmeric Dicils of the Type R.CHCOH),
0"
Cri."s pub. Llect. czecho3l. chem. commun., 1958, 23,
No 71 1237-1251
A h. a t r a c tSee RZhKhim, 1958, 1+3207,
Card:
thosyethylene-
14-tritylserime (III), 1-trityl-2-carbOme
imine (1-,[), j.,hich on reaction -vith -jH2~H.Ha gives
Cara 1/ 10

CZEC'i0SLG!MYJA/0rgan-ic rMemistry. Naturally Occurring 3ubstances
and their Synthetic Aiialogs. -3
G
Abs Jcur: Referat Zhur-ia,-imiya, iTo 4, 1953, 11467.
hydrcamic acid (V); the latter adds HCI with the forma-
tion of the hydrochloride of 3, -amino- '-" -chl oropropichy-
Iroxamic acid (VI); strongly basic anioa exchange re-
sins cyclize VI to I. For comparison pur-Doses 4-benzyl-
aziiae- (IX) and 4-oenzhydz7laminoisocxazolidone-3 M
were synthesized frt~m N-benzyl-2-carbomethoxyethyleneimine
(VII) and N-oenzhydryl-2-carbomethoxyethyleneimine (IIIII)
by the same method. 1-benzylethyleneimine-2-carbehy-
droxarnic acid (XI) is synthesized by refluxing 87.5 gms
of the methyl ester of 1,2-dibromopropioric acid rsic-1
in 550 ml C6H6 for 3 hrs with 71.4 gms triethylamine and
36.2 gms benzylamine, shaking the mixture with water for
12 hrs and allowing the mixture to stand with VII ~Tiq:
meaning appears ga:eole_q for 48 hrs, 6btained by eva-
Card : 2/1,,~
cz-ECH0G'L0VAKL,k/Cr,ganic Chemistry. iraturally Occurring ---ubstances
aiid their Synthetic knalogs. G-3
Abs Jour. Referat ZE-ur-nimiYa, NO 4, 1958., L140/7.
pcrating the benzene solution with cold (50) hYdroXYl-
amir.e (p--,~pared frcr- 49.6 gms of the hydrochloride of
hydxoxy-'a--r.ine i-, 250 ml CT13 OH and 24.6 gms Na in 300 M!
CH3("'~ in 50 m! CH30H, fo3-lcwed by evaporation to 200 MI
at, 20 . -,I is isolated by dilutitIn with water and neu-
tralization with cH CM)HY yield 73.61t', mp 154-1550 (frem
qqr'~ alcollol For ~roo-f of structure 0.3 gm XI is hydr-
1. and the product
genated over 0.2 9M PtO in 10 MI CH30c""
'? : 1) HC1 (acid); paper
is refluxed for 3 hrs with 5 ml (I
chi-omatographY using the system phenol-water-PPH 3has es-
tablished the presence of alanine (XTI) and . 4.1anine
(7 : 3) in the reaction mixture. Dry HCI gas is Passed
0 into 20 gms .1 in 2CO mil benzene, f ollcwe(i
~or 30 man at 0
Card 3/ 10
Ch +-- ---y-
emistry.
.atliyall~ ccurin- Subs ances
and their Synthetic Pnalogs. G-3
Abs jour: Referat Zhur-Khimiya, wo 4, 1953, 11467.
by saturation at 200. The addition (after 24 hrs) n-A
C
2
.0 rrl ether res-alts in the prec~Ritation of an 82
m4xture of the hydrochlorides of,/- -benzylamano-,; -
chlorcpropiohydroxa~-Ic acid (XIII) ~yield "4.5(,-, =P
184-1850 (deccmp from C-q3o-")
0 ) and -benzylaXCJno-X-
chloro-propiohydroxamic acid (XIV) (yield 16.3','y IT
1450 (deccrm,; from CH30H.-ether)). XIII (like XI)
gives XII and XIV affords < -XII. Cn standing for
12 hrs and refluxing for I hr with trimethylamine (in
(C:130-") XIII gives XI (yield A mix'ture of 17.8
grs XIII in 700 ml CH3 OH and a solution of 15.7 9M .'Ta2CC3
in 1.2 liter of water (prepared at 00) is allowed to stand
4 days (20-50); xi (24.8() precipitates; the filtrate
4 'L
is evaporated to 30 TQ a~ 400 and acidified .,Tith 101,11
Card 4/ lo
Chemistry. 114aturally Cccurring -Substances
and their "Syntheti-c Analogs. G-3
Abs Jour: Rc.-ferat 7hur-il,,imiya, 1ro 4, 1953, 11467.
CH3CCCH in 50', alcohol to PH 6; !X precipitates (28(,".
YiL-W, -P 1540 (fron; 991,' alcohol). Aen the latter
over PtC? and re-
product is hydrogenated in CH3CC'OH
th
fluxed for 3 rrs wit (1 : 1) HC1 acid, serine is
olit-ained'.. A mi:-~ture (prepared at l0c) of 30'.0" gms
E,i-.-nvhyr.'.cyIamine, 40.4 gms triethylamine, and 0.2 mol
of the n-~thyl ester of 1,2-dibromopropicnic Csic 7
acid in 350 ml abs benzene is refluxed 4 hrs, the
benzena solution is washed with water and evaporated;
the yield of VIII is 83c,', mP 100 .5-101' (from benzene)
When a mixture of 11.1 gms benzhydrylam-ine anci 6.8 gms
liCethylpiperidine and 10 gms of the methyl ester of
v -broncacrylic acid in 50 ml benzene is refluxed for
2 hrs, the yield of VIII is 941".. A mixture of 0.3 mol
Card 5/10
VIII is allowed to stand for 3 days with a solution
of hydrcxylLne (prepared from 45.5 gms 14H20H - HC1 in
3CG ml CH3 OR and 22.2 gms ITa in 250 ml C~~-3011 at 150), the
mixture is diluted with 1 liter water and neutralized
with CH3G'0CH; the yield of 1-benzhydrylethyleneimine-
2-carbohydroxrric acid (XnI) is 96ci" mp 157-1600 (decoMP;
from benzene). The hydrochloride ofa-benzhydrylaminn-
-chlororropiohydroxamic acid XVI) is prepared by
saturating a suspension of 0,1 mol XV in ?-CC ml benzene
with HU gas and allowing the reaction mixture to stand
12 hrs; the yield is 4-j"j', mp 176-178' (deccm; from
I - -N - -- v-xrT (likp XT) gives XTT. On re-

CZEECH05LC%rA_,:IA/CrZ,anic (hemistry. Tiaturally Occurring Substances
ana their Synthetic hnalegs. G-3
Ab S T ur: Referat 7hur-Yhimiya, iio 4, 1958, 11467.
el
0.5 liter rl13()i~ vith 12.5 =s Pla2C03 in I liter water,
tn stard 4 days, and acid-ifying with 50 ml 0
(iH30YIh in 2CO ml alcohol; the Yield is 73r" X-P 139-141
(d-_~eon,p.. from CH7-30H). Fydrogenation and hydrolysis of
the lat~ar rrna"U'C"t give serir-e. The hydrogenation of
0 .03 mrol X in jC0 ml alcohol and I ml CF3COCHI over
F~Op by 800 Tr-I H2 gives 2-15 gms of the amide of N-
ben~I~ydrylserine, n2p 142-1440 (frcm alcohol). A mixture
0'.-- 0.03 mol ILI, 50 iril dry -nyridine, and 2.5 Ma. mesYl chlc-
ride is ke-ot 241 hrs at 0.4 diluted with 2CO ml water
and CHC13; III is extracted in 901- yield, mp 12-3 (from
benzene-alcohol) 0-CI mol II in 50 ml dioxane is mixed
with 1"120H (prepared frcm 14 gms MH2.011I.EC1 in 1CO ml abs
Card VIC
CZECTI0SWVAKIA/0rganic chemistry. Naturally Occurring SuIb-
stances and their Synthetic Anajooys. G-3
0
Abs Jour: Referat Zhur-I(himiya, 110 4, 1958, il467.
"'I-qOH and 6.9 gns Ha in 30 ra
th' CH30F'); after 3 days
e reaction mixture is diluted with 100 ml water,
and neutralized with CH3COCH; further dilution re-
sults in the formation of a precipitate (33 ons)
of 1-1 -tri tylserinehydrcxami c acid, rm 1090 (c.-,jgF.);
the product contains 1 mclecule of crxibined CH30H.
A mixture of 0.02 mol HI, 20 ml C61T6, 1 ml CH3CH,
and 2.5 gms !T-ethylpiperi dine is refluxed 8 hrs.,
diluted with 15 ml CHU washed with water, and
evaporated; the yield 0? 1
IV is 80"', mP 30-131"
(from benzpne-cyclnheyAne). (r, standing for 3 days
a r4lixture Of 0 .18 Mol IV in 100 ml d:io;:,ane end
1
25 - 2 gns "'M-201' - RCI and 12.4 gms Na in 150 m! Cjf30H
Card 8/1-0
'IZECHCSTLCVAKIA/:0rganic Chemistry. Naturally Occurring SuIb-
stances and their Synthetic Analogs. G-3
kas Jour: Referat Zhur-Khimiya, INO 4, 1958, 11467.
is diluted with water and neutralized with 03CCOH;
V prea~Lpitates, yield. 941., MP 138-i4cio (from 10 : I
benzene alcohol). ;L trityl- 1,)-chloropropiohydrox-
amic acid is obtained by mixing 0.05 mol V in 2DO ml.
abs-CH."l3 with a soluticn of I mcl ECI in 25 ml ether
at 700 and OvaPorating the solution at 400, the yield
is P-D 120-1240 (from Cqj~S) (hydrogenation and
hydrolysis both give XII). 4~ -trityl-amino- ,~ -chloro-
propionhydroxamic acid (1.6 gms) precipitates from the
mother liquor follow-ing dilution with 50 ml- cyajohex-
ane, xp 133-1360; hydrogenation and hydrolysis give
-XII. A sus-cension of 0.1 mol V in a mixture of
100 ml CHC1 3 and 200 ml C6H6 is saturated with HC1
Card 9/10
card 10/10

CZECIICSLr,VAKIA/Organic Chemistry. Theoretical and General
questions on Organic Chemistry. G-1
Abs Jour: Ref Zhur-Khirl.,, No 13., 1958., 43207.
Author Zumn Petr, _,iicher Jiri, Y
,rupicka Josef, Svoboda
Hiroslav.
Inst
Title Stereochemical Studies. VII. Oxidation of Diastereo-
isomeric Diols of RCH(OH)CH(OH)RI Type with Periodate.
Orig Pub: Chen. listy, 1957, 51, No 6, lo68-ioft.
Abstract: Polarographic study (see Commication VI, RZhKhim,
1956, 78180) of the rate of oxidation of nine pairs
of acyclic diols of RCH(OH)CHOHR' type with periodate
at different pH (2-7.9) and diol concentration
(6 - 10 '~ - 9 - 10- ~ M). Investigated were
ethylene glycol (I), threo- and erythro-isomers of
Card 1/3

Tic'

il. J-
C L-.!!
ca.,

r: ly :3
arl
J.

~c
'e ccyc-

.,.a r su I, e c

82211.1
R 12~ 3
ld 2 i 4 2 -
P. yi-
.,BD,
on';
i..
0,
t 2:, 0
M.,Q
rl
-po-
170- 4-71
3/
G-7

12,
07
IC,
- -ans
br
-
il-111 ut at
()I
A I
rL
(D'fLL
Z ID
in zl
ZO

Oc

G-O

p-.7 PU '3
C~ Oi it,

01
'

f-c
17~-173

l~
nrio s si-I c
O
c onf I rU r t i
C
3

c 0 1 Oll
--- 1s f0[,
L; ~r

7-1 n-';' cc n'-yOr-ine -incdt -conhv-
r ne (-,!n
7_ 1 -1 '1
(",zechuslovakia,
no. 11, "lov. 19'5P
0- 1~ n 'A
-1, july 1,,5 ti. cl S.

r r rl C-~- I rn
f'nn i.
Vnj. no.
TILIV
JQ ~~C. Unclis.

"1 -1 7-. 71
si:,e and configuraticn an tyke
rate of intramolecul!-Lr cyclJ-z,-ttJ on ~":'e 'T-tll -I-- n n'-% ~l "erivaTA-ves of cis-
-tr6 ans m~ n ocycli nrl s (Tn -1 s h)
C-7 vo,,y', - ~
Tr ol. V), npf'. 1050
(7, Irr ,,o. 7, Jidv 1~,59, linclas.
-A .

l"'m lilt flimp, !111
i .0 U R
C

a

3Y
of
L:1 r

7

c
c. 2. 1t C!r n

;)e r (-
~,d
_
C CI_
C,:
L
a of
;id r r) 7 "i 1 S- and
t:,ar_--ACC) Up o n h e t:c
' tl,
0
e sa;~ie
Oxj--E:r~ o-er :ia ir. c nrod!-.
c- Sl
I

W - ie C,
ri C, 3 7 nly 2--all a-
:
-unts
.
-
o T-
!;CC f) . Cis- ~;nd :raris-ACC
a r a t chringed ane anotlier by
the fcllm!~rE, cIL,-

C,~ : p
e _ 3 ,: Recrys-
_
tal- -z:. vfc);-~ ol
-he y
leld
q the les

.23 .
s
s

)1 1
o
v,
T-

-1 e c
u:) -lenzoyl,:tion of the
res)_(~L.r 1-ft af'ter rec-.- al."vritiori
. I : t, L J_ L
-ur( -es o~ cj
0 e r a t% - ls-and
ACC, immcr.
'eaction, Of
H!"; C.-ove cal:..ses -.Ii~-ratioll
O.L --nun, and'
_z-elir tc; the
C)" L.ians-0_benzoyl-A-%G.
t' r Hydrolysis
1-J-- Llttcr yiold-s trafis-AC0. C-
-AC0 mw,
',-,e transfor,-.-..-d trans-,').CC by
ci
-ACC, with CH S02CI 7
a, sub-seouent- c~ cl-iza _T
tion, _n K pres-
cnee of CFj-.c_1,,~1,, of the c i S! 1-
Cz0choslovakia.
r!
UP'.
l)+12
produc d 1-. nt 0
-71
into trans-AGO b-
Cl .1
-IY-7rcll-YsiSL D: T-rans-ACIO may be ob-
~-;y t.'Ac cyclization of
Cyclizat-Jon of the latter vjith SOCI
yield.-, -t-rans-1-1G, -urh_-cj:-, n-ay be subseijUe-tl~
1.YV. E: trans-ACO iLl -also -,--.,.,nthc--
z)~ reacclin~; cis-1,~1_cr1cxycyclnncs with
CiS-ACC :ray be prelpared from trrm5-ACC
ethods ana 6-ou3 t o C anel D , in -w! iich
intemedi~ite prot2uctsj trans- 111-benzclyl-
and cis-F0 are f!~.-rmed.

"LL

r e

17
f b ta, i

rv, 1 a tzn
n 5 -
, ,
17
7
-92- -e)
aq. tr- a s
12
r rj!:. aq. -a"-C.5; -ral r VI

8/`3
-;nnS-V-, TT
trar~s-.",, 102-103
T. 4 4-
.,J.P.:-. - -.-I -?ttej m.p.

COUNTRY Czecho lo-,iakia
T 1 T L6,'
7110 2
G-2
A B S T T',_4T14heri ACC was reactc-.d d14,.',l
ti, - u P-1i02C(,H~COC1,
e co:~respondixigr IN-substituted ACO %~.rc"g ob-
a inv. d Uist-ed below are ACO's 1'rom TurbUch
?n7,oyl derivatives were repared,
anu in OC of the erivativeS
ci:3-III 128-12c.4.5 (from a1c.); trars-I, 185-
187 (rrom a1c-);
c-'s-III, 141-142 (4-.on a1c.); trans-III, 164-
(from.alc.)-
Cis- 130-131 (from benzene); trans-IVt
155-156 (from benzene)
--s-VI 13" (from berizene) $ trans-V, 137-138
(from benzene);

R C
J OUR, T~h i-,,i
0
711+12

A DS I IR iC, T J s t; ol ACC. -If
C,
-
-
rnin it NO
a V t -1- 17 00

V:

7q
f CH-,Wc

etl a
tr
("ron
~,.Ce aiC, -TIJ
-- I
l
11; c j 0 120-121 ('rom E-
J,
l -
~
y
t e - r: a T'r 'rls- 1
01-m
.
5- 13 'Tr~-T, ethYlacetatel
t
. r
,
ar
A. 1. M
1 C) ( fro: ethylace T
,v
tate) c i
-
s

rr"m baflnf':.'Yle- PC- tr. e th. s-

Vi.7- 1, i 13
(T'
-r,)m et!
etF-, t e) rars

5'
'fro'-
',-!Cetp~te) .

3,) 4-
cthy.--jacetat. I,
1. 1 ej; trans-
12 7 ot~rylacetate); c--4---U,,
i2l ( f rom trans-IX,
f;l 117 119 ( f r, z: ethyl--. c e tat o) 42-
p c -t' trans-Z,
f~~rcm "HjlCC,;H::; . -tr. ( 11
J~) !00-101 CA /O~- FO's were b
o
t.)irc,~! b-.v Of, N-betizoyl-AOD
met!lanezulfonatos witil 0.25 g of
Ch,CCOK in 150 ml o alcohol for 16 hour's.
12/23

li 0
j G 7-; p ?o
'T
1:60ow sire 'he ,nnpired b-
(_'2r
T t T -.)-tCrza-Les n OC: c~. -,-2-,-hc-nyl-47
C ~L.S_XT 1
144- fro:~-- a I cohol) trans-X'l
I 7Z 51~_ "CIV tr. eth. and
(f rom
I!_-)-171 Urnn'. alc .
T
~,-, -3
n~ 17 1 e 11 e - _,I 0'.-Ei ZCI_lln e(C71 s I T
ra ns - 1 . 1 -5-/'0 . 1 169 (f rom aic .
t -ny" !lp_42_oj-.n7
c- a:7 e
17~5-115t_ (fro:: aic.),
trEins-_, lill)__il_'./l().M-.f 155-11 (fro-
aic .

T
2 0
r,
2 t t v ln n _oxazol-ine
1~';4-1.i5 (from alc
t r.--i ns -T (77 Yiehl) 132-1,"'/0-li -2 - 11
c 1 L - 2- oherllri-4, ncn,-v7i;itLl-iy! e -~e-
Tetr- 174-175 (frc.--n aic.
7t.p. fr:~m.petr. etl~
-J!Ll~ (fron a1c.); cis-2-phem
y
L _r,,7~-2-oxazoline, --cf I
d e c a m p- t hy (Cis-
r,~-tr. ~-th. 54-55, 1--,3-161+ f r -.m.
.17 fr-rl ,,c-tr. etn
115- 11" -$ 167-"LE;8 (j'rr)m a1c.
> 11 ine (cis--7111)~
5 unlecametli-r.v -0--azol-,

cl
-joctylarn`ne, m.p.
r'~, i! ben_,,ene) is lfor:,red at- the
Tratiz-? .-.bcnzovl-V a n4
c trans-
L~i. p I'rorzi pet'. C-th. ]T
t;, ~vtc- anrartaxftly of a ml Xture
nnd a
up"n boili-n~- VvK-!, 155, f1cl. Fols are char-
actt,erize:d bly the meltInr r)oints of kcrown
obtain--d via c,-;.nde,'sa-tlm-I of ACO
Ai- ,'Ine reaction Con-
-*
r 4 C_ f0 _11~Cle tram-N-benzoyl-
d

y
y
T:
5:4
Y JL e
ben zrjyl--7
tral"173- N
Y
1- T r'r n:7. Yield)

PLI-3
714-12
C~
A -Ls
A
fol"
Yiel
1 510crclodecano-
197-1~80 (from
rem4 ne- un-
r 1~
ndi 1~ on s'
L
C
o, ,nd
WAS
from w~'-ich by r-avl~rso !rarration
2 j:z-alft:~ of
f-)T:.c
-1 LCY
r -be-L
t V-

c -c-c i icuslo vail,
C A
;!D 71li-12
-3 J ou
:T L

P--
- -nitrolt-)enzoyl-I"'.-Cl)
-
O
_i
j
2 P1,2, P ~Eilir,-
-r)
t.
trans-0-p,
- ,
0 ICci-i9l. ';'r ci m 37
1
lz
f 0
!--CI
fDyl-
I ~, nr._,~_oxime (CrIV-
;Clodecal-101-2-. e
O C-
etll-ylacetate and benzene
on thir rpductlon
-
~
tai;icd u
o
,
:
,
ere
i
cH tol~etl;er uritli a smali
and trans
re I --
b

--the
'
ale.
*
-b6nzoy
,
,'
om ale N
(W (f
!%:I c r1~,:- ..4-2
~
r
.
'
:-----~,_ -
3T )H1
On' so c
r c

we.mmmmm~

J7-
7
her, j-F-,
v
1143,3 w"AL Ca
Lri 1. 'a I 1 0 .1 C)
T I
--C 11C
I n T., de C..
t. 2. a
a r. r,, 'c. a j! YIf
i&_n je,-k~Ij ~c,
r r, Wa S -J 1
a c a r.,
f L, of
'a if r u:m 4_qf~0/10 m:
C. r) 9
'c* - -T)
Czechoslovakia
1) 0
uS. j0u'R. -~ k. Z

le I d b p 13 0 - 1 3 0/ 1 5MMI Trars-III

,.V,3 c i S- 1 epoxycy -_'I ot rid ecanP4 (z-,J_s-VII)
L L,
=.'4. Trans-!"
e ll+-1-142^/l'
-
~d o 1-he formation of cis-l,;!'fep0-,YcYcI0-
ex --decane (ciq-VIII) (34% yield, t..-p
121-1220/0.1, mnm) Ci s-V was trans 4% --)r;ed
(o-~-r ac .iO Alo0j) into trans- 3. , 2-Cyclod PcanP_
_*1 (trans )0 (PrCM th.
Whi,e~ C-LS I nd c s - VII I up o n
h-ur boilin,, With 80,1, dioxane i-n tbe -cres-

few drops of HC10 wIera_ so -trans-
ence Of
,
$3
1
c"
vc.
r
0
orined into trans-1,9-

110. 2~ 0 19 r)
? 1 13
313T ~DUI C T befizene-petr. eth.) -snd c-~s-XII, n.p.
i1--"140 (fro-:: petr. eth.). The results
p.~.Ovc- that the initiel AG has a
C~: in -ndd-"Aon t r i e; , h (-. w
of 10-and 12-
transition --"ntc antiDara7 I el
C 0 T - i a r a t o r is difficult. The latter is
'-,t~cessary --or heformation. of -'I-rans-three-
m;'-zxibi?red 'Ll-ans-axides are formed
easily onlY frum the amn:oriiun bases of
large ring AC. The struct',al-e of cis- and
tzans-XI (not described before) w--s C-'- It k C'~ C-TE
517 on the basis of variations of the rates of

-T7
CT
In -JA J~ 7
t,t1W,- "'n
62', 7
7L
na
Cct
q.
ion
f, '.1-00n
,ut-It jr-n
r in,
f,2
V ajnE7 3 dorl V tive 3
ro
to clo -jrc-lre clll<
of
deriva-~ivl)s f
of
ep
constrMt
is 'imilli-f,
ks c Pre
rdenc- di
re~ponrtir.,- ("Ope

-T
E
TIVI. C T
t, d
3A:-!D:
62175
'hydroFen bonds,
t
'the formation 31L which is inf-Pluenced priwLri
1y by reelprocal reniotienes.9 oi' lIC-and
;'~Vollps. T"he Value of.ApKla [PKIa(cis,=i)I~1a,
,v.-an3)] is a ralativo uoasure of t~alo roraotA
ne3s. Tlfte valuc-;8 ofAplr,-a slioj, that in rings
whic'n :-..re 3mallar than nirie-memberad ones.,
pis-isomcr for.'as a hydrogen bridge easler
than trans-isomer. Beginning with cyclononan
the hydroSen bridge formed easier in tran.
3/8

110 `-1 i?,
7U.13.
m o
--:--- j-j,yij-
;,j re- 4
nes- !C)- find ll~)-
A ,
j,
I rl

r

J. r I c o'a r"L

t
-
0--c
i

s
he
t
t'lle mixture 0~
j
rs-i,
CC; and turs
.2; -~ -ae r P

are i7iveilt: 57
t r .7 -17
Ci 7
2 2
2 15 f 0~1
13, 16
r ISS,
8
1
8 6 o r, n
10

C AT 17~ G 0 R I
JOUIR. 23 I-J'59, "1175
T- T' T' LE
C, 7:~ jl~l . I I Tj
P.:T~ JT RA T
e r---i in. e,'~ p f c, r c s - v n. r1 t rk~ n s s of
of .i~e
a t 1,3 fl f 10--i
_-.rl an
of I -'n
C" f azld'
bo ir
nl of cyc-
(II) is 0 b t a i E" d ia p
t
in, 130". aqueoij7 m~:,V-y, 3 1, 0 4,,
-
I- -_j u
thylone g-col with o.1 solu-
tion of

C

iq C, J,
R;- Kh

1^1T
u
AC

C T cr. f
to 0
b-
3 o
]OW
alo I
),
y 0
--
nd S t" i
~)Cyj
_COjT, Ye"O-
t ai s-2-s-Ini-In0c, -
t-rar-
a inod f
n
-
..I
f
(hr, 'i-irs of boil-11"S 7c
a-MLP-O -

b.p.
'
~ (ro:
L) from
127-129
P-1 p-
01
101 -
a1c
.
1
.1 -
(frola
-l
n 100
ethyla.
m.
-m
is-2-d
the

"A-ZD- 7/6

Big of
At S the cu. an
Sta reochaiialcal stu- .- - -L! d
de';.ol and Y2
n"ocyclopentadec-
traiis-2-aminocyclotatm a
Anol. U-ifto -_LJ.W, and -Jiff Siche~r
Oesko :T, ekem, usty 52, IU51--d
Mslov-akad. ved, Prag-
r .--11 -Hydrogenating it voln. of 1W
53 51.
d. CA.
g, cyclotetradecanol-2-one oxime In 11. EtOH aver Adams:
g5 *s.2-aminocyclotetradecanot
,catalyst es 21 01
Zcgit, EtOH), HCI Oft, m. 223-4
rtc,.(On Boiling 18 bra. a soln. of 18.0 g. Irams-2-
Aen-yl,.4."odecamethylene-Al-OX"Oline 16 250 ml. EtOH,
and Boo ml. coned. HO gives 12-2 fraiss-2-arninocyclo-
11
tetradeennol (U), m. 10"0 (petr. ther): HO salt, M.,
215-1C10 (EtOH-Et%O). Similarly Is obtained &-2-Mb2*-.
:cyclopentademnot, in. 89~-W- (petr. ether, I*cdne); Mli
rans-2-AminocyclOw. 1
salt, m. 220-2.84 EtOH-EtgO). I
tadecRnol, -- - 282% yield from ka-2- henyl4,5-tii-
-3.5' Pctr- ether)-
-thYIene-ALOx&zOILne, m. 93 F,
decamL
HO salt, M. 192-3* MOH-EtO). Adding 16.0 g. X#OH
ml. H%0 to a soLn. of 18.2 q. I In 500 tal. CJi4 anti,
tn 250
'then 114.6 9. BzC1 portionwtse w1th stirring and cooling
gives 2.5.7 C. cis-2-benz=ldocyclotetradecELnot (M), M.
183-4* (EtOl-1). Similarly are obtained: SUM Irans-2-
.benzamidocyclotetradecanol. In- 170-1" (FtOH);- 90%,
til-2-benzamidocyclop-tadecanol, m. 142-2.50 (MerCO);'
;83% trans-2,benzaTnidocyclopentad~m-,Inol, in. 143-3.5*
(MeXO-EtOH). Acylation according i-1 the method de-
:scribed in C.A. 53, 11859, yields cis-Z-(P-DitrOben"mido)-
,cyclotetmdecanol, m. 194.5-5.0- (EtOH) I---2-(P-nitrc1-
:benzamido)cyclotetradecanol, rn. 192-3* IMOH), cis-20-
nitrobenzamido,Ncyclopent-adera 0-1., m. 162.5-3.5- MOM,
GW
and Ira mi-24p-n I troben
W011). A cooled soln. of 23.2 g. M In 400 nil, CgllpN
-ernight. the inixt. dild
kept with 16 9. McSOXI at 0' av
with Ice 110, the crystals filtered off. washed, and dried give3,
2g.o g. cis - 2 - lienzanddocyclotetradecyl methanesitIforiate
(IV). in. 14F-D* (AcOHO. Similarly am obtained: 07%
fraw-2-benzanildocyclotetradecyl metlumesulfonate, m. 129-
30*; 100% cis-2-benmmidocyc-loptn-ta-dt-cy-I -methavaulfo.
nate, m. 120-1% and 91.5% Irans-2-benzamldocyclopenta~
decyl methanesulfonate, m. 107-8'. Hcating 30 bra. a
soin. of 20.0 S. crude IV and 20 g. anhyd. AcOK in 15M ml.
EtOH to 95' In a glass autoclave, distg. the EtOH, and extg.
Ahe product with RtlO gives 19.05 g. trans-2-phenyl4,5-
'dodecamethylene-Al-oxazollne, ba."., 190-200*, m. 02-3*
ether). plemte, tn. 189-601 MOM. Analogously
are obtained; 72 cis-2-pbenyl4,"odemmethylent-Lit-
5 1. (Et
oxazollne, m. 95--8 (petr, ether) (picrute, m. 160-
~OH)); 95.6% trant-2-phenyl4,5-tridecamthylene-4l.-oxa.
bo 180-90', m. 47-8*
Apetr, ether) (picmte, m.
14i::6b- 'rM.OH)), and 91.67o cU-?-phenyI4,5-trIdeca-;
meth lene-41L-oxazolline, be., 195-202*, m. 68.5-V (petr.
ethers; picrate. m. 136.5-7* MeOH). When the N-acyl
derivs. of the above aminoc & Is am subjected to acyl-
mIgMtIon (N - 0) by dissoging 7550 mg. of the c,.pd. 1, 4
nil. dioxane satd. In the cold with H-, the mixt. kept at
room temp. overnight, dild. with 5 ml. dry Et.0 and at-
lowed to stand overnight, the soln. contg. the cis isomers
remains unchanged. whereas the trans Isomers yield cryst~
HCI salts of the following compds : Ira=-2-benzoyl Xy-
c)-clotetradecyla mine, in. 171-3% g*,~,%s-2-(,1uitrobe=o y1-;
oxy)cyclatetradecvlamine, m. 173-5% Ira?U-2-brnzoyloxy~
cyclopentadecylamine, in. 106.5-7'. and trans-2-(P-nitro-r~,,
benzoyloxy)cyclopentadecylamine, m. 170-81'.
L. 1. Mrb&nek

A
XVV. Dissociation constanta
of cUlollaxwecarboalle acidsiYand cyclohaxylamines and
conformational equilibrVA.-W. Tich:~, J. jonK and J.-
Sicher (U. akad. v6d, Pi~~gue). Collection Czechost9--
-M-Y-W.-Communs. 24. 3434-41(1969); cf. C-A. 53, 21161i.-
The fM_ energy difference between the axial and equatorial
form was found to be 1.6 =1: 0.3 kcal. for the free, and 2-2 A:
0.3 kcal. for the ionized carboxyl group In the following
acids: cyclohexanecarboxylic (1), cis- and trans-4-methyl-
cyelohc,,~anecarboxyllc (11, M), cis-, and trans-3-terl-butyl-
6yelollexanecarboxylic (IV, V), and cis- and trans-4-tert-
butyleyclohe=necarboxylic (VI, VII). The calens. were
made on tht basis of measurements of he dissocn. consts. in
.80% Mcthyl Cellosolve using TV, V, VI, and VII as "axial
and equatorial standards." Similar, though not so con-'
elusive, data were collected from cycloheiylamines: cyclo-
~Ilexyl (VIII), cis- and Ira nr4-meth y1cyclohexyl (IX, X).
:and cii- and Ira ris4-kri-butylcyclohexyl (XI, XH). I,from
-C% and C,H,,MgBr, m. 31-20 (petr. ether at
-Hydrogenation of p~NfeCoH4COSH
in AcOR Saver Pt0j) [it:
-0.5".
45`~`and atm. pressure afforded 11 bla 130.0 . m. 2S
_~,j%fe3CCjj4AC (-,t3 g.) added with stirring tit 60* to a
-INaORr soln. prepd. from 1.1-1 g. NaOH and 2j0 S. Br ill 1200
mi. Hto, tile temp. allowed to rise io W, kept at 956 for
min., the mixt. dild. with H:O, extd. with Et-0. treated
~v~jth S02, uidified with HCI, and the product filtered and
i i NIe1CC4H4C(
crystd. gave 62 (8070) ),H, tn. 165-8*
o9ellatell Over
~(Iigrinc). TI,is tl~0 g.)'hY1r1( Pto, ill AcOH

&ve3.2g.VI,m.117.5--i8,tfro'm-ittoH.Ciii,,a-ndAcc)L.*t,
successively); Me ester (from VI and CHIN2) b, 102-3*, iijO
1.4557. Combined mother liquors train the crystn. of VI
evapd. to dryness, dissolved in 60 nil. (CH1011),, rtfluxed
7 hirs. with 20 g. KOH, the mixt. dild. with Sit) nil. 11,0,
~ ~A-
"t4i

rrl
acidified with HCl, arid the se
V, protlact crystd. fr
C41-14 gave JA g. VU, in. 175.&-0 . Hydrogt-ciati,ut of .10
f-
P-AcNHCjf.Me in 100 ml. AcOll avcr 4 g. PtQ~ at 65 ,
46tn. of the product ut 105-9* at U.J nini., and cry!,t:r.
0 train cyclohexane, 2 from Cslla) gave 2.3 g.
deriv. of X, m. 140.5-l'; refluiting widi lIC1 aff6rded 0_5, "
X, b. 145-6*, nj? 1.41509; 1ICI salt in. 260.5-1.5' (1-:1
MejC0); Dz deriv. m. 180-0.5' (aq. EtOll). Fr(-.;ri io~-.
mother liquors, after the crysm. of X, 2.5 g. Awel~`, t!ef7
of IX, in. 08.".5' (cycloltextuic and C.114) was ,bfaia.
Hydrolysis Wave IX, b. 1.113-70, 00 I.-I&SA; 21121 ~al~ :11.
u
,
4
233-4
MOH-Ale,CO); Bz deriv. Ill. 1:11 ,i-0.5
WWII).
V1 (2.28 g.) In 30 Mi. coacd. Iltso. and 15 fill. C1104.
treated at 40~5* duritig 30 fain. with 2.7 g. VaNs with
stirring, heated for 30 juin. tit 50". the ulLxt, poured Oil ice,
the aq. layer extd. wfth Et,o, alkali4C(l with K011. tile
I
liberated base extd. with Et!o. and Vic ext. dried (MgS
04)
' .4
t
~Wl
, r%* MOM;
and distd. gave 1.4 g. (73.7%) XI, bit 70-S
*
'
-1
(r- 1011).
(1110); Uz ilcriv. in. 15-
HC1 salt tn. 280, .7,5 t..
MA-6-6041/'d - X11,_
14048; HC1 salt in. 311-12' (EtOll); Bz deriv. M. 1A)-
0:5* (McCO). The dissocn. conts. in 90% Me ecflo~ Ive
a
;-
at 20* (pK,') for I through XII were: 7.43, 7.66, 7.42, 4 Al,~
7.06, 7.0 1, 7.43, 9.51, 9.4-1. 9,5A). 9.2-4. 0M.

SICHER,-J.: WSHER, M.; RUDINGHR, T.; ECKSTBIN, M.; SORM. F.
Amino acids and peptides. XXVIII. ~7nthssis of threc- and erythro-
d i-,V,-iamino-,mP,-hydroxybutyric acid (r-aminothreonine and -r-aulno-
allotCreonine). In Rnglish. Coll.Cs.Chem. 24 no-110719-3729 N 159.
(Mul 91- 5)
1. Department of Organic Synthesis, Institut of Chemistry, Czechos-
lovak Academy of Science, Prague. 2. On leave of absence from the Medi-
cal AcademW, Krakow, Poland (for Eckstein).
(Amino acids) (Peptides) (Allothreenine) (Amino group)
(Threonine)

- SI-CHERI J.; SIPOSY F.; JONAS, J.
Stereochemical studies. XVIII. Syntbesis and dissociation constmit -
of cis- and transaycloheptane 1,2-dicarboxy-lic acids, Coll Cz chm 26
no.1:262-275 Ja 161. (EUI 10:9)
1. Institute of Organic Chemistry and Biochemistry, C2echoolovak
Academy of Science, Prague.
(Stereochemistry) (Cycloheptanedicarboxylic acid)
(Cycloictanediecarboxylic acid.

SICHER J.- SIPOS, F.; TIGHY, M.
.L~
Stereochemical studies. XIX. Confor-mational studies on the 2-amim-
4-t-butyleyelohexanols; synthesis of the four atereoloomera. Coll
Cz Chem 26 no.3:847-866 Mr 161. (]MAI 10:9)
1. Institute of Organic Chemistry and Biochemistry, Czechoslovak
Academy of Science, Prague.
(Aminobutylcyelohexanol)

MARES, F.; ROGEK, J.; SICHER, J.
The chromic acid oxidation of cycloparaffins; correlation between
reactivity and thermochemical strain, and notes on reaction mechanism.
Col-I Cz Chem 26 no.9:2355-2369 '61.
1. Institute of Organic Chemistry and Biochemistry, Czechoslovak
Academy of Sciences, Prague.
(Chromic acid) (Cycloalkanes)

o
f, il Lj-, p t i "t t jl i~
Q ~~l roups
2 1
m. v no
j 0 11 T P
ri -
f Al
e r

0 c ta
A ~j c 1
r1 r
11'r
r., ti a ~j
r) o-,i
.ci. v
tj ril,

E, 0
c,, n r e a c. ton r. ti~ w Pen
Z. i e the Ogous
z3a -71 e r ea C ti on
1, n r F, cozi,;,%,uer the I-act
f 11 C, t hi a i n t in e c a s
r:: th~_- forma-
71 th"6 of I ;s is
QC .3 C'. L oC o
r ii r f r vi ri t. hi. s fr by
P ~11 the ~-H nu an, d e
vely
0 (t f.-anp-! the
Lhf~ raLio bet-Noell
13

j.3 ~3

31/62 '000/021/o 10 ~06`)
'310C /
'~tereochcmical researcri ... B156/B101

-owever, as ethanolysis al' -tert-butyl-2-methyl-cyclo-
4

-.ox~-nol and certain
*,,ions show I
it has a higher-

.r a I .; o To 0.01 mol2s 1' ',r, Iert-buLyIcyc-,D-
benzamido-4-t
d;s3olved in '1~) :ri ;i.-
xa i i c 'L ~-m.02 mole of freshly distill 0-7-
ILa lie su lonylchloritje the whole is held at Ooc Vr_--
6 12 hr and diluted sitt, are filtered of--,. ariu.
ilf~-.Ijhed in water and .)ercentage yields and inell-in:;
points, in OC, of the 1! 78, 93 94; IV 76,

26.5 - '27 'from ethyl acet_-.' 135 - 134 (from ethyl acetate'
f3r the production of 1II, RZhKhim, 1962, abstract 12Zh'?,
.-i,a 1 t i ng point 140 - 1410G. C 1V dissolved in 100 ml absc-lWe
~cohol ia heated witri O.C,- 'il for 70 hrs at 9,500; the
u S C, C i i , i a f i I t e r e d o f I' a n cohol, the filtrate evaporatlr--~,L
il V cu6. and the res;aue
et er -and an aqueous Nal
h CO :3
P
r,ion; the ether extracts
and dried. the o 11
Of
i~parated, 1.05 g is analy;.t::, ._-.-p!iicalIy orr neutral Al 20 5' C,
nd 0 respectively, :.f' ~,~d 6-benzamido-4-t ert -buty c -
tj
;~t~xene-l (VI and VII), 5
16

5/06 11621000/02 1/010/06~~j
and traces of
wasned ouL with C -H
tne sctme condiLlan~~
z~-,pavated amounts to i . li~-j
L i L u ,.) n., (I L U o .' 2 ) t'
Complete tranLlll~At.10:1.
1-cyclohexanol acetaz~--
--t.risnolysis of V is carri,;~i
continues for 23 hro
lon on neutial Al 203 has
-.
VIII, and 5 % Ix. 6u
6/6

SICHER, J.; ZAVADA, J.; SVOBODA, M.
Stereochemical studies Part 22: Bromine addition to medium ring
cycld6lefins; a transa~nvi~r reaction. 6W Cz Chem 27 no.8:1927-1938
Ag 162.
1. Institute of Organic Chemistry and Biochemistry# Czechoslovak
Academy of Sciences, Prague.

SIPOS, F; KRUPI&A, J; TICHY', Mi; SICHER, J.
Czechoslovakia
CZECKELOVAKIA
Institute of Organic Chemistry and Biochemistry,
Czechoslovak Academy of Science -- Prague'- (for
all)
Prague, Collection of Czechoslovak Chemical Communi-
cations, No 9, 1962, py, 2079 =2OBT-
7-
"Stereochemical Studies. XXIII. The 4-t-Butyl-2-
Methylcyclohexanols -- Synthesis and Rates of
Chromic Acid Oxidation."

TiChT, 1%; SIMS, J.; SICHM, J. CS"A
Institute of Orgmic Chemist--y and Biochemistr7, Czechoslovak Acad%W of
Science, Prague (for aU)
Prague, Collection of Czechoslovak Chemical Umunications No 12i 1962,
pp 2907-T9-M- .. . I
"Stereochomical Studies. XXrV. A Study of Ring %formations in 2-AwAnocyclo-
hexanol Derivatives by Spectroscopic Intramolecular 4dmpn Bond
Doterminationm
C-V

SMUR, J. - C~~- ST, M. GAULT, Y. ; 1~ -E LK-M, H.
G ~- -,R
no acade-mic degrees indicated
Institute of Organic Chen, '--stry and BiochenII-sta-yj Czechoslovak -',-cadxny
of Sciencey rrague, and C.N.R.S. Institute -for Chemistry of Raw
1.4teri,als (Institut deu Substances Naturelles), CTif-sur-Yvette,
France (for all)
Prague, Coll.ection of Czechosiova]c Qlemcal Commmica;..ions fio 1, 1963,
Pp 7241a
"btereochemical StLidies, EN.
Dias tere6igomeric `-Hyaro3qphenyl and --.qydro:golefin Derivatives:
Assignment of Configuration by Spectroscopic Intramolecular HydroSen
Bond Determination"
Y)

'SIGHER J CHEREST, M.; GAULT, Y., FELKIN, H.
~ ~' ~J- *
Stereochemical studies. Ft. 25. Coll Cz Chem 28 no.1:72-81 Ja 163.
1. Institute of Organic Chemi'stry and Biochemistry, Czechoslovak
,Academy of Sciences, Prague and C.N.R.S. Institut de Cl~mie des
Substances Naturelles, Gif"suf-~Yvette, France.

-2-
CZEC~~*OSLOVAFIA
ZAVADA, J; KRUPICKA, J; SICIM-R, J.
Inutitute of Organic Chemistry and Biochemistry of the
Czechoslovak Academy of Sciences, Prague (for all)
Prague Collection of Czechoslovak Chemical Communications,
N; 7, 1~)63, pp 1b64-1673
I'Stereochemical Studies. XKVI. Determination of the Stereo-
chemistry of Vicinal DibromideB by rolarographic
Reduction."

SICHER, J.; 1"ICHY, !!.; SiPOSY F.; SVOBODAI 1'~%; jONAS, J.
Stereochemical stadies. Ft. 28. Coin Cz c iem 29 no.7:1561-1576
il 164.
1. Instituteof Organi~3 Chemistry and Biochemistry, Czechoslovak
Akademy of Sciences, Prague.

PA I K 07, A
z he :: 30 n r, ~ 2: "' 8P,4 1
oE C-1-ganic Chemistry and Bi3chemistry of the
L., Frag-.e. Submitted Deceriber

t , 32 .rl,~~Il ';z Chem 3," nc . 2 : 4,28-
Ir,.-t-'t-ute of Organic Chami3try and Biochemistry of the
h ( mi nG
zec -s")vak Acaderry of Scintmes, Prague. Sub tted Jii , 30,
C
lq64 ~,

oar

F; Slauao 4T
T'7 .03L0
20% VALIA
Institute of Orgivaic Ohmistry and Slo
Cz"hoaloVok Aaadomy of PragW all)
An as Am"Mi
callms amblalL
mo juTYM. vv ajwp-zwp
",3terftchml*A :3tudiono P&rt 38s ConrOrmt1aml orArgloo
for the fadol.-ematertnt abanV In dlfform* cyc4abox,11
sy-Stmoo 6

SICHERL, B.
"Heat transfer through radiation. Introduction into technical
practice" b~r Heinz Reinders. Reviewed by B. Sicherl. Rud met
zbor no.1:84 162.

SICHERL, B.
"Dispersion of fusible fast particles with ultrasound" b~r Klaus
Stwnm. Reviewed by B. Sicherl. Rud met Zbor no.1:56 162.

PAVKO, D.; (JCl-,J-'EKl Di-rigo, dr. Inz., docenL; S.;
S~q_HFRL, B,; 11,; PAULIN, A.; GOROP, I'll.;
GAZAFURA, K.; VI-H-RGAFi, F.; AHLIN, F.; FAW;1C, J.;
KERMIG, Vlktor, prof. dr. inz.; GGGALA, A.; RAMOVS, A.;
SKUBIC , 'r.
New books. lil met zbor no. 2:189-216
1. Chief Editor, "Rudar3ko-metalurski zbornik" (ft.r Kersnic,
Viktor) .

PAVY.C.1, Dragotin, dr. inz., izredni profesor; SICHERLY Bogdan, inz.
Fhe heat and 6ec-nIcal studies of open-hearth furnaces.
Rud met zbor no. 2: 1-1-1-123 t63.
1. Oddelek za nnonLanistiko, Liublianal Askereeva 20.

C I II z ..I
_1 11 '__ '.r
SICHEROV, P.S.
--- - __
Rapid, high-efficiency slicinp of sugar beets. Sakh.prom.11
no.9:26-29 S 157. (MIRA 10:12)
1. Moskovskiy tekhnologicheskiy institut pishchevoy progyahlennosti.
(Sugar induatry--Zquipment and supnlies)

SICHEV, V.V.
Entropic effects In three-dimenstoml hypernonic ,,,an flow,'3
around slightly blunted bodies. Archiw mech 16 no.2:517-
519 64.
1. Institifte of Mechanics, Technical *jniversity, Moscow.

SICFI,'VA M. F-. and FEDCROV, A. S.
"Fe=ite Storage for the 13ESM Computer" 1957.
publ. by Inst. Exact Mechanics and Computing Techniques. Acad. Sci. LZSF.

KARCHEMSKIY, M.Yu,;kand.tekhn.nauk; SICHEVOY, A.I., inzh.
Preparing prestressed floors with wire-mesh reinforcement
in Dnepropetrovsk. Bet. i zhel.-bet. no.4:175-177 AP 61.
(MIRA 14:6)
(Prestressed concrete)

GRECHKIN, 9,A,; SIGHEVOY, A.P.; BREZHNEV, L.A.
Reddijigning some units of the 120 mill at the Dzerahinskii Plant.
Met. i gornorud. prom. no. 2336 Mr-Ap 164. (MIRA 17:9)

7- ",,:J

NEFEDOV, A.A.; BREZHNEV, L.A.; SICHEVOY, A.P.; BYSTRIKOV, O.P,,,
HILIMAN, Ye.A.
Studying the deformation of metal rransverse helical rolling.
Stall 24 no.53429-432 My 164. (MIRA 17:12)
1. Dneprodzerzhinskiy metallurgicheakiy zavod-vtuz i
Dneprovskiy metallurgicheskiy zavod im. Dzerzhinskogo.

Bli'UVOYJ- S.M.; SAVINTSEV, R.I.- HiLIMAN, Ye.A.
7 - oun
. he!L--a: a:IJ the ap~p7l-a'lan of d periodic
~~ 7 no-2-c:l F 165.
(MIRA 18134)

20 1 -1 i I
G-PLECHKIN, N.A.; U7AFFENKO, ~-I.j.;_p-,HEVOY, BETIK, V,T.;
BFEMNEV, L.A.
Tnoculating rollin=g mdll w.-th add-ition allOys by electric
-;r)tj.r,k, prr - 2--l" 78 Mr-Ap 16~~.
s. M('!t- i gornorud. om. no.. . - , , -, (WIL-1 IF: 5)

~~ i, p - GAVRII,~~T~;, A.3.,, NIVHMAT, 1-1#
1-0)
Ir
r)p,.r.if~, ~,, .01. 1 i,.Ig loa, 1 1 .
jr,t-roducimg the .. I- , s3f th.? V.,-~D m;i'-Il fo:, r
Met". 1 gornfarad. prm. no,3,-8041 my-Jo 165. (ML-f-A Ist LI)

SICH-VVOY, P.S.
Method and apparatus for determining consette quality. Sakh.prom.
29 no.6:23-25 155. (KLPA 9:1)
(Sugar industry)

SICHEVOY P S
, .- ~O- 0 wt-' -f - i -
Improving cossette qualit7 b7 redesigning best slicer )mives.
Sakh.prom-30 no.2:17-23 F 156. (MIRA 9--7)
1.MTIPP
(Sugar industry-Equipment and supplies)

SICHI?VOY, F.S.
-
Theor7 of slicing high-quality sugar-beet cossettes. Sakh.prom.30 no.O:
37-41 Je '56. (MLRA 9-9)
1.Moskovskiy tekhnologicheakiy institut pishchevoy promyshlennosti.
(Sur.ar industry)

SICHEVOY, P.S.
IMMEMOMMINOW
Qiality criterion for coseettes with rectangular cross section
Sakh. prom. 31 no.2:53-56 IP '57. (MM i0:4)
1. Nookovskly tekhnologicheskiy institut pishchevoy promyshlennoett.
(Supr beets)

Sigm.oTir ~m*-
I
I
1W Now method for checking the quality of beet cossettes. Akkh. prom6
32 no.3:30-32 Mr 158. (KXU 11:4)
1, Moskovskly tekhnologlaheskiy Institut pishchavoy prosrehlonnosti,
(Sugar beets)