(SANITIZED)SOVIET PAPERS ON ORGANOPHOSPHOROUS COMPOUNDS(SANITIZED)

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP80T00246A011800070001-3
• Release Decision: RIPPUB
• Original Classification: S
• Document Page Count: 26
• Document Creation Date: December 22, 2016
• Document Release Date: August 25, 2009
• Sequence Number: 1
• Publication Date: November 28, 1960
• Content Type: REPORT

 _1 L
/ Approved For Release 2009/08/25: CIA-RDP80T00246A011800070001-3
u/ C44Fers of unsaturated phosphonous acids. 0 t~
N). I. Kabachnik, Be N. Tsvetkov and Chzhan Zhun Tui (inst. Hotero--org. Coapds
Moscow). Doklady Akad. Nauk b.S,S.R.
Addn. of CH2SCHMgBr soln. (from 0.65
tetrahydrofuran) at -60? to 0.6 mole
followed by removal of the solvent in vacuo, adda.of 300 al. petr. other
and 1.3 moles pyridine (to cleave the complex between Mg halide and the
(
P ester), removal of the ppt, and distn. in the presence of hydroquinono
gave CH2:CHP(ODu)2, We b2 49-51.5?, nD0 1.4471, d20 0.9039. Similarly,
HC1CMgBr (of..Jonas at at., J.Chea.Soc. 1956, 4765) gave 74% HCICP(OBu)2,
b2 58.8-60?, 1.4520, 0.9289. Reaction of 0.3 mole BuOH and 0.3 mole PhNBt
131, 1334-7 (1960).
at. Mgr 0.67 mole CH2:CHBr and SOO al.
(du0)2PC1 in 200 at. tetrahydrofuran,
added in petr. other to 0.3 mole PhPC12 in petr, other at -30? and stirred
1 hr. gave 62% PhP(OBu)Cl, b2 77-8?, 1,5352, 1.1049. This with CH2:CHMgBr,
as above, gave CH2sCHPPh(O3u), 66.4%, b2 76-7?, 1.5310, 0.9762. Reaction
of (BtO)2PC1 with p-CH2:CHC6H4MgCC1 (ef.Leebrick et at. J.Org.Chen.23,935
(1958)) gave similarly 33% p-CH2:CHC6H4P(OBt)2, b2 96.5-7?, 1.5398, 1.0251
(NaNO2 was used as the inhibitor during distn.). Treatment of the neutral
esters with, l.1 mole H2O contg. 4% H2S04 in dioxane at room temp. 0.5 hr*
gave:.92% CH2SCHP(O)(H)OBu, b2 S0-lo, 1.4479, 1.0040; 78% HCICP(0)(H)OBu,
b1.5 65-6?, 1.4492, 1.0322. I and S in Bt20 at 0? gave 88.2% C112sCHP(S)
(O0u)2, b2.5 96.2-6.8?, 1.4730, 0.9954. I and Mel in potr, ether in auto-
clavo 4 hra. at 100-10? in the presence of hydroquinone gave 84% CH2sCH-
P(O)(Me)OBu, b2 64-4.2?, 1.4452, 0.9862. I heated with cyclopentadiene
diner in scaled tube 13 hints.. at 190-200? gave 55.5% di-Ou bicyclo-(1,2,2)-
2-hepten-6-ylfkbphosphona2r, b105 99.7-101? 1.4792, 0.9696, which with S
at room temp, gave 63.5% corresponding thiophosphonate RP(S)(OBu)2, b2 139-
9.2?, 1.4969, 1.0425. The unsatd, esters of the above series polymerize
readily on being heated without inhibitors. The reaction of Mel and I
resulted only in polymerization of I if the solvent nett. ether was omitted
or replaced by excess Mel or MMCN.
 ki. 1. tcabachnik,
1lo0cow). 12veot.
A. N. Shilov and W. A. tluctryukova (Inat. 11otoro-org. Coupde.
Akad. Ntak ;;. $? ., Utdol. Khio. hauk 1960, 146.
113P02 roacto cioothly in tho cold with diazoalkanos yielding the corroopon-
ding octoro; exile one ^olo of diasoalkane reacts regardless of the ant.
Thus were propd. (Wo0)P(0)112, b2.5 25-5.5?, nn0 1.4275,
analcgi b2 31-2?, 1.4250, 1.1120. Both esters doconpposo
top-3 they cryotallizo at about -200, and can
oxidize in air and .are hydrolysed by 1120. They
of 113L'O2. This confirms the covalent structure
be stored at -60?. They
show gqual. teats typical
oP 110P(0)W2?
 OIFJanolithium compounds in, the synthesis of estora of alkyl and aryl phos-
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phonous acids.
No 1. Kabachnik and U. N. Ssvotkov (Inst. 17otero-org.Ccmpda., I4obcow).
Ievost. Akad. Nauk S.3.S.R., Otdel. Khim. Ncu k 1960, 133-4. Cf. Doklady Akad.
Nauk Lis -W 117, 817 (1957).
A11 reactions were run under N2. A sole, of PrLi from 35 g. PrBr and 5 g. Li
in 150 al. Rt20 was added dropwiso at -60? to 42.5 g. (3u0)2PC1 in 100 cal.
Bt20; 6t20 wan then removed in vacuo and the roniduo was treated with 200 ml.
petr. other and the solid was dopd. Cistn. of the"11q. portion gave 605
(Ou0)2PPr, bl 59-60?, n101.4375, d20 0.8836. Similarly l3utiand (3u0)2PC1
gave 813 (DuO)2POu, h1.5 70.5-1.5?, 1.4421, 0.8814. (Et0)2PC? and LiPh gave
56.53 Phf(oat)2, bl 63-5?, 1.5113, 1.0235. Indenyllitlaium gave 64.5:5
di-Bt 1-indenylphosphonito, b1.5 99-9.5?, 1..5491, 1.0655;; similar reaction
with RG4jOr gave but 40;5 yield. 9-Fluorenyllithiun (Gilman at al. J. Org.Chcn.
23, 550 (1958)) in tetrahydrofuran similarly gave 785$ di-9t 9-fluoronylpho-
sphonite, b2 148.5-9?, M. 67.5-70? (after Sublimation at 2 mm). Similar
reaction of Rt7gBr gave only fluorene and a trace of the above ca or.
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7
Crgennic in~3c dGs, ;fly. 3;/.nthesis of alkyl aryl chlorothiophoophatea
end alicy. aryl thicpruw~iiornr+_idc~c.
Ifel'n5.kov, Ya. U. ilakanova arid G. Zaks (tea. Inst.
i'ertillzor
y
env
Inoectorusl32cilce, lur. Obahehei xhim. 29, 8288-8
(1959), of. this 2473 (1959); GO .'ut. 337003(0.:1. 8448 (lobe)).
Addn. of l0F8Cl2 (0,1 Tl.?19) at -100 to C.1 sale drOt7 aril 0
11 mol
i''
.
d
t3N in
1yh01 over 0.5-1.0 !jr.. .stirring 10 ,rin. longer, and quenching in E20, gavo
the followiDS (N0) (.4rO)p30.1 (..R and Ar shown reap.) :,'t rb g
20 o ' . 5 n, b pg..g0~
d20 1.%,499, ~j 1.5390; .Et, p-C1C6$4, 6O , b0 9 lazI- , 1.30042 1.05520;
Et, c.,4-C1,0bH30, 58$, b.).4 133-70, 1.43800 1.5600; 8t, 2,4,5-.G1 JC6f 00 ''
50
b 163-80 1 554 , ?
c0.7 , . _fi 1.5031; fit, b-Q,111c h4' 54?x, b0.2 1600, 1.45439 1.5740.
.5L ti1erly (110) (Ar0).>xaCi werc pre' d. by stirring 0.1 male ArOPti012 with 1-4
u-oler ROi3 4-10 hrs. at 20-300, follo*.ved by an ea. treatment; the host 'ylalds
resulted from the use of 20-30 moles .#M par mole or the chloride; if run
In 06% or I')Cl, the reaction alsc g good yields with 10:1 molar ratio
of raeotentsi the fbllovri.ng were c.cepd. by this nothod: Rt,tt; Et, P-0 ?TC Ii
The products reaoted with various aminas in 5-10 ?yrs. at 6-20o. in 1,t202or6 4'
06116, yieldlne, the following(R0) (Ar0)Pv"'1t" (2, Art R', !t" Pt:or?n roop. ):
iio, p-02z4C6aa4, "s Ott tindistillablel, 69r, d20 1.30F36, n~0 1.5700; 'Tt, P-O2IJ-
o6h4, 4;t, Gt, 08, , b0 158-640, m. 340 ti
.1 f Zt . p-02110 6II4 , Vol ?63, 5?`,,', b0.2
153-.",O", 1.2406. 1.5930; St, p-02I4u6H4, I!, Ph, bti.2 165-700, 1.%:o63, 1.5720,
589.x; ft:, it, k;t, 1t, 70;.,, b0'4 120-20, 1.1475, 1.52.38. The 2nd, i5rd an' 4th
of these artides provefa to he equivalent to (3to)?1'
C?C0NOG-p In insecticidal
ectivity against: the rice ;voovil.
 Or1afi6 insectofnn.3iciftoS. XLVX? than' F-3 o? so-no i4arifatiVSS of Pho$P!1-
Gnoacatle 3oid.
And . Y. LoflRk' flt1 (Ben. :31st. Vc"tili-
*
WWI.
.1. 1:sR rf7H1
td. ia. : el'IIiaov, YS,. ?9 3239-~1.(195').
7rlei .
Shur.
and Zr-sectofung1,0100S, ~.oaaa~r;) ? . Obshc?~oi
r9 7130.("55); t=-:9 at. 500,340;
of pruced. abaft. U;,-iet. 2,701,225(0?n ' tiry~ (1956);
., t~rl.t. S ~ t.
GbiSia, 9, 47 (14335};. Brit., Fat. 725,653 (0?A. 50,
E3rit.tat. 782897 (C.u.520 619,1(3.956)0
7g7,~25 (C.A. 51, .13x756 (1057) ; ,
vtit~ aProprl.e.to
P n
bra follortin? oomp es, were props. by interaction of (t0)5
the reaction boirig 00^P1-,
uorivs. of cbloroaoetic or chlorothloacetic sold, 8=. 1:1382.
0 330), P(O)CBr00` t, b0.2 115-201. c0
4ted by 4-10 hrs. at 100-50 0 (. 115-2000 1.1456, .1.4632, 364;
I2U 1 x580, (r 't0)1'(0)Gh2 GO u '? b v??16
1, (u) Old
2 U r =a 4990, 5G,;.;
C1-P. bC.3 152-4 , 1.257.,, 1.
(ZtU) 2= (G } Jii?UU2v (1 4
b 70'xc; (3tO)2P(0)01120Q208fC j013 2,9,-
1 5231,
,
CC#C64Cl-P, 0., . 143.5? , 1.S485
11 (V )6h2CUc c 2 Cl, -2,4,51 b0.2
5, b0.1 139 41?. 1.3u17, 1?"183, 45`ta;(,5~0)Z t d '! 1.09e%4
c
(?? 0) 1=(0)t111?C(i14t,, bU.l 123-9 , '
169-Cie, 1.4131, 1.348L, 50."
6i Vic. ''h3
j 174_7", 1.1.6+12 , 1,52450
1.4686, ?.Gsecticl~EAs
caters end the ataidas of PLnsphonoacets0 acid P active contact and
thu catars~.cf pnoephonOthi00o?tic acid wove vox.
but .
of t1e aromatic esters.
systemic iUZgcticides, this being speoiolly true
 o,. ,..,..,,.A r,., o,.i,.-,^ onno,nQn~ rioonoQnTmmA conl 1Qnmmr)nn1 ? 'n . /~
74-4
a. Qrann-0 t n
`~
.
- '- '..';t'C~~ti11 C. Gl,y'1..li:t In which
one 11 atom is also replaced by Cl yielding Cn112nCl2P?OCI2 i;~oducts after
treatment with S02 (of. above ref.)
 Approved For Release 2009/08/25 : CIA-RDP80T00246AO11800070001-3 Qz.
r n I i
Diaryl esters of N-phosphoric aci4. of anidines of the aromatic series.
G. I. Derkaoh and A. V. Itirsanov (Inst. Ora. Chom., Kiev). Zhur. Obshohei
Ihiu. 29, 342d -S (1959), of. 29, 241(1959).
:aln. of C.H. soloe of RCC1:PiP(0)(OR')2with NHH3 over 3,hra, at 20-300 and
koaping the oloood vessel 10-12 hrs. at rooa temp. gave after removal of the
nolvant and washing the residue with warn H.O. 63-100N RC(FI12):NFO"(0R')2
which ca bo orystd. Orom LtOII. Thus wore propd.:(R and R, shown rosy.)
(I)
Ph, rho m. 99-1010; p-C1C3H40 Ph, m. 147-90; p-02I:C6II4, Ph, no 168-700;
m-02EC6114, Ph, m., 128-300; 3,5-(02I7)2C6173, Ph, in. 182-3?; Ph, 1-C10#I79 me
119-21?. 0imilar reaction with Zt2M in IIt20 gave RC(IdEt2):PO(ORQ)2:
Ph, t$, in. 77-90; p-C1C6H4, Pb, m. 69-710; l>-02NC6It4, Ph, m. 102-40;
m-0E0, Ph, in. 100-2?; 23H 3,5-(02n)206II3, Fh, m. 99-100?. Dimilar roactiox,
with Ih[IPI2, completed by rofluflnS the C6I36 or P$Cl soln. (latter used for
the nitro substituted members) gave 110(I IFh):Po(OrI')Z? Fh, Ph, me 153-50;
P-C1C6II4, Ph, m. 192-30; P-02I3C%f4, It, m. 195-60; m-02I.C6II4, Ph, m. 204-b ;
3,5-(02I3)2C6II3, Ph, m. 164-50; It, p-02NC6H?, a. 153-50; p-C1C6H4, p-021-
CgH4, m. 225-6o; P-02}J06H4, P-02i:C6l4, m. 232-3 ; a-02U061I4? P-021
m. 172-40; 3,5-(02I1)20aH3{~ P-O2J06II4, m. 210-120. Pyrolysis of I at
270-000 in vaouo gave 72io (PhO)2i0Iu22, which distils and solitlifiao; in.
144-G?; 58w FnCIV also formed. Similarly II gave 91t+ PhCLJ and Wl
(Ph0)Zt01M&h, m. 127-90. Compds. of typo I end-the Noll-diethyl analogs
form oily IICi salts on bean, treated with dry H01y these salts regenerate
the original materials on being 'treated with aloe ITaOUI.
 Approved For Release 2009/08/25 : CIA-RDP80T00246A011800070001-3 Ca.rluo ,
i
or
vativoa of nitrobonzonesulfonanido-N-phoaphot?ic acids.
a. V. hirsanov and N. G. Foshchonko (Inst. Org. Clton., Kiev). Shur.
()behcltoi lchi^. 29, 4085-91 (1959). Cf. 28,339(1958).
Treatment of 02NC6H4so2N:PC13 in C6!!6 with Ile2t"' with ice cooling gave
after the untako of 6 moles of the a")ine, evern. of the rvlvent and tradtinl
the residue with a little H209 and cryctn, of the raoidue frog, cnall vol.
oP r.te;H, the following amides, similar reaction with Bt211H was perfr,rmod
at roflun over 8 hrs.: o-O2IRC61J4So2NSP(pmie2) 3' 863, ra. 160-3?; n-ieoner,
76;3, ,a. 66-8?; p-isonorI 79,', n. 109-11?; 0-02IVC611 4U42tti:P(NSt2) `c.1 9N,
a. 84-6?; p-iscnor, 98U, n,'58-60?; the m-isomer wao an unpi%rifiiablo oil,
The, 9t2N7 derivo, Could not be rnnvortod to thr. trianid3o avsn after 40 hrs0
of ru;luxing, with the arsine, nor could the C1 nton be hydrolyzed with
allcaii. Koe'luxing the NO members with ac;. ale. NaCli gavc3 so:~:e 20-5S3 start-
itt Uatu:aialo, 61-3a O2NC61i4LU2NHPO(NMo22 and 315 nitrobefaonesulfonanides.
The o-nitro member failed to hydrolyze at all even after nany hrs, React-
ion of 02NC6H4so21filt'oca2 with 33,E ace.
by ovapn. in vacuo and treatment with
rtf(;;rloz)z, a. 161-4?; m- ir.3cner,
Linilarly were propd.I p-U2NC6It4S02NH 0(NBt2)2,
79;,9 m. 125-7?, Who o-isoctor could not be
hhoee anideo are col,
aaction of 0.06 saolo
NoNi1 in diosnne at 25?, followed
SN ticl gave: 82;, o-02NC6ll4SO2NH-
sa. 145-7?; p-iSRr_13r, 84E, n. 169-70?.
in.
109-11?; n-iaoror,
obtained in the pure state.
are titrated ac.monoba.ic acids.
iieUf ivith 0.02 mold 02 NC6H4502N11P0C1
fellotrcd by ovapn, and Dither learhinr; with 1120 or oxxtn. with hot t:toli,
gave: 70,3 o-02NC6114S02N}Ja1'U(0?Io).9 70;.;, n. 156-8?; 13-1socer, dihydrate,
79,, m. 195-8?; p-isozmnr dihydrato, 83u, ca. 186-90?.
with jirONa in dioaano Q;avo: 763 o-02NC6UI.1l3~JNano(0n'h)2, n. 164-7? (tri-
hydrate); cu-lsonor, 823, trihydr tc , m. 137-400; p-i oner, 94:x, anhyr;rotts,
?
n. 210-12
; analogous di-p-chlorophonyl ester ors n-isoiev,
n. t82-40; of n-iconor, 5955, trihydrato, n. 153-5?; of p-iroL:or,
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2
anhydrous, n. 221-2?; analogous o-nitrophonyi eater of: o-isosaor, 92);,
anhydrous (an arc3 all remaining in this list), n. 200-2?; of ra-isomer,
90'j, n. 172-4?; of p-iconar, 33'3, :n. 24)2-5?; analogous p-nitrophonyl
esters ofs o-isonor, (3i. , n. 21.0-3?; of s:i-irunur, 87j~, n. 216-8?; of p-
isomer, 83r, n. 220-2?. These Na salts raadily pans into the Ot2O layer
durin!s ostn. of aq. soln. with E:t20, thr?ay atao dissntvra In CC14 and C6g16,
provided that the eotor, is:s based on the p-6hlorophonyl resicilie; the
othoro are insol. in ore. solvents. '
 V. 1. Chevchonko and V. T. Stratienko (RZ)tallurg. In?t.i IDnepropatrovuk);
#hur. Obshchoi IChin. 29, 3757-60 (1959). of. 29, 345E (1959).
Passage of dry NH3 into a benzene soln. of ArSO2NIPPhCl2 at io-15? gave
ArSO2PJsPPh(HH2)2 (Ar shown)s 90.7; Ph, a. 151-20; 94.9N o-t C6114, o. 140-
92.653 p-isomer, in. 130-1?; 91.65 p-C1C6114, m. 162-4?; 94.52 l-CIO 1i7, m.
149-51?; 97.2;3 2-C1011 7, m. 140-52 0. Heating those with 0.214 aq. IaaOI3 O. S
hre on a steam both gave PhP(0)(IJH2)OIJa, needloa, n. 164-5? (from aq.Btou).
Similar hydrolysis in acid medium gave the corresponding ArCO2fail 2, and
the P-contg. component was not onaninod. The above dianidos are not attuckod
by hot neutral H2O. It is cugtgostod that the diamides, like tin einilar
triamidos, have a chelated or hydrogen bonded ring structure at the ICH2 and
1302 groups; in the compds. described above the P-N dipole is diascainatod
in the Ph ring, oxfllaining the relative hydrolytic stability; the triani2es
do not have, such v dissipation of the dipole and are very racd ily hydrolyzed.
r
.O .,Wo . i-.I
I. t
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 t--, ,Jc I
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V. I. Chevchenko and V. T. 'tratienko ('Letallurg. Inst., Dnepropetrovsk).
Zhur. Obshchei Ith im. 20, 3458-62 (1959). of. 29, 1005(1989)0
Rofluxing 0.003 mole Ar30`N:PPh012 with 0.013 mole !-h&732 in C6116 5.8 hrs.,
follo;vod by oepn. of Phi3i2.TiC1 and washing with H2O and IT :'a0H, Savo the
residue of ArSO2N:PPh(NEi'-h)2 in 70-96;) yields: Or sho.sn) : '"n, in.
1p10;
O 3CeH4, a. 1060; p-isomer, ft. 1820; 1-C10H7, .in. 2070; 2-010H7, M. ';].50;
o-021106:34, in. 2120; m-isomer, M. 2140; p-isomer, in. 1760.= a Wash liquors
gavo,on boinS acidified aS 2, soma ArSO IMO(Ph) (ijn) formed by the
2(II)
hydrolysis of intermediate ArS02N:Pi-ih(EZifh)C1 whioh scare not isolated.
I (Ar shown): Ph, in. 1670; 1-020137, M. 1600; o-02PIC6II4, M. 1650; n-isomer,
m; 169?; p-isomer, in. 1660. If ArS02IT:PPh012 reacts with but 2 moles PhI I2
in 06Fi6 (2-3 hrs. at roflux), the monoohlorides II appaar in the resulting
l-rylaminolysis of -phonyldiohlorono,.~hazosulfonaryle.
.Ppt. and on treatment with aq. I,aOH are hydrolyzed as ebove to the anilices.
The derive, with Ih and 1-C10H7 radicals are sol. in 06H6 and remain in
coin. The replacement of the 2nd 01 atom in II is difficult and even after
prolonged roflux, some II remains unreactod in mists. with ''hig32; this
lack of reactivity is ascribed to steno effects. flefluxin,^ ArSO2iJ:Plh-
(NiTFh)2 with aq. ale. 14aUH 8 hra. gave come unreaotcd'insol. icatorial and
acidification gave the expected I (Ar shown) in 37-67;) yields: Ph, n, 167?;
1-ClOH79 M. l000; o=L:oC6*;4, M. 1040; p-homer, in. 1600; 2-CIOH7, r!. 134g.
The o-tolyl and 1-naphthyl members rcmuire.21!i?CiH for this hydrolysis,
while the others are formod by 0.211 I3'aO:I; while the nitrophenyl members
evidently undergo such alJ line hydrolysis readily, the anilides could not
be isolated as tar formation intervened. Tho.relative stability to hydrol?
ysic shown by o-substitutad tolyl member is explainal by possible hydrogen
bonding of the Ile group with the Sow group.
 Approved For Release 2009/08/25 : CIA-RDP80T00246AO11800070001-3
Preparation and properties of dialkylpho+:pheta ulkyl n nathatoo.
t4, 5. tlalinovskii and ;. F. Coloe_-to (&t.sto Univ., Lneprorel;rovak). Zhur.
Obshchoi Khin. 30, 652-3 (1960).
cf. U.b.?et,. 2668826-32 (1955), G.A. 49, :5517 (x955).
floating ottuinolar ni,zt. of IZOC52K with (!i0)220C1 in flt20 2-3 has.
the following producto after sepn. of tC1, (P.'0)2P(0)s2COR (1'.' and R thorn
reap.) s 86.4;.' fit, ?Io, b5 511.?, nt0 1.4915, dx0 2..17929 lit, Lt, 84.55 , h4
59-60?, 1.4715, 1. L43; bt, Pr, 89.5;0, b4 79-90?, 1.4860, 1.1072; 7'r, tIc:,
99.6W (thie and the following ostorc were 'aatdittilluble), nu0 1.4520, '720
1.0949;. Pr, St,,1.4665, 1.1080; 3r, Pr, 1.4729, 1.0873; Pr, 1so-L'r, 1.4575,
1.0590; Pr, Cu, 1.4620, 1.0655; Pr, iao-Ru, 1.4602, 1.0363; ?r, An, 1.4508,
1.0070; Pr, iao-10,.1.4360, 0.9680; iso-Pm, ?a, 1.4490, 0.565; iso-Pr, 13t,
1.4565, 1.0892; iso-Pr, Pr, 1.4615, 1.0695; iao-Pr, iuv-Pr, 1.4470, 1.0531;
iao-Pr, 1119 1.4605, 0.9895;,ino-Pr, 1130-But 1.4555, 1.0125; 1uo-1'r, An,
1.4465, 1.0312; iso-Pr, iro-EMi, 1.4337, 1.0078. Lopor,iil'icjatioa with .t1c.
IJaOa or KO3 in 24 hrs. yields :C pr Ma pitouphate and is or Na ;,anthat; i.,
 Approved For Release 2009/08/25 : CIA-RDP80T00246AO11800070001-3
Synthesis of acyl derivatives of 0,0-dibutyl thiophospliate:
S. P; Olifirenko, N. I. Zerlyanskii and A. M. Lylyk (State Univ., Lvov).
Zhur. Obshchei Khim. 30, 579-80 (1960), cf. Michalski at al.,Rocx. Cher.
27, 482 (1953).
To 10.5 g. Na in C6116 was added 82 g. (Bu0)2PH0 and after 20 hrs. the excess
Na was removed and the rixt. treated with 14.7 g. 8 and heated 0.5 hr. to
60~; partial evapn. gave (BuO)2PSONa, hygroscopic solid. This treated with
appropriate acyl chlorides in Bt20 and refluxed briefly gave the followings
(BuO)2PSOBx, 41%, nol 1.5015, d21 1.066; (BuO)2PSOC0(CH2)2CO2P(2)(OBu)2, 351?
d21 1.466; (CH2)3[C02P(S)(OBu)2]2, 78%, d21 1.158; (CH2)4[C02P(S)(O9u)2]2,
26.57, d21 1.1192. The products were distd. at 0.4 ma. but b.pts. are not
shown.
 ,irbuzov rearran'>.rut cut of vinyl, t:t,tcr. c of p';o.rphorou:> arc'. phenyiphoorhono,ts
at -I d r.
I. I~. 1.tttst:nlto :.77 it ti. +? :fir ilitlti (t:. ~:.;.,GLIen QGt3{/ ti'i;U Univ.., ?.o ecw). 1I
Lukl:.dy ,J:ad. :+rnuc '~... ,S , 13'=, list-tt (ag1i0).::i'. ti iU j..124,12.5t (11I59). I
Lufiiuting 8.2 g. (Et 0)2POC!IICH2 with 7.7 iloI 4 hrs. RTave 655 '.tl and
89 lu,)'i3(t);ii:)(GCt1:Cli2), b25 82-3?, 11 1..4265, d20 1.0775. (3rtO)2PCC11:C112
(10.0 c;.) and 10 t;. 43,t.i in 3 lira. at 1500 in sel::oc2 tunic 1; zvo 85; U4u1.'O-
(OUu)(OCU:C142), bl U3.5-40, 1.4369, 9.9786. (CIi7:C110)2Pt'tnt (10 r;.) mid
12 g. Prue in u :trs. at ilC? gavn C`'shj ilet'0(0Cll:t,1:2)2 , 1)6 5 6^.5-`3?, 1.!',388,
1.1030. iitOP(O(;AIoICld7)2 and ""tl in 6 lire. at 130? gave 8: ctro(l:Ctio:l; l?
b2 69.5-70?, 1.4470, 1.0392. (ihtO)21'CC ItCH2 ;nd .tcGi icel?t 2 11a~r gave
u3 t1c; J(G.at) (QCr t ;ids), b2 72.5?, 1.4352, 1.1310. ';: C1 caul :iu.On(CC1S;t:11
2)2
in 8 hrs. at 120 gave O Oa^Q(vC :12'::2)2, i>1 1154?, 1.5315,. 1.1961.
.(he following are also r;aportsd aw prupi.. Awlla'ly a':. 00-4C?:
(OC111C11q), 90r:, b8 79-9.5?, 1.4290, 1.04171 '..;e'1J(C'3u)(OCli:C1i2), 86"?, b1.5
79. 5-60?, 1.4320, 1.0232; i:tPC(G1u) (C'CI1:Cls2), 50'i:. t.)7. 51 95-6?, 1.4335,
1.0070; Lt