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March 5, 1999
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/ Reactil4WW4EIVeftekiMea1391919/99ilkhedik-WW*PRIIPIIIMAPWars of halogen substituted aliphatic welds. 0,7elmei ewe V.L,Kukhtin (3.M.X1rov Ghem.Teohnol.Inst.,Kazan), D kled kee, Nauk o.lt, 91, 837-9(1953). CPYRGHT The reaotion ot UeQ)3P with Me02CCH01C2O1 yields mainly (MS0) CO2ms, U21015-80, do01.2691? 4?1.4535. The similar reeotion of (Rt0) Pat 110-20? yields meinly (Et0)2P(0)011(OH 01)00 lie, b4151-20 d: 1.1882, 0 d801.1706, 1.4460, along with some mitmotritstLe 142(bis-diethylphospho- no)proi,anoote. The reaction of AtO 00/1010H Cl with (Lt0) PONa gave exclu- sively the latter product, (MO) (0)01100 ile)CH P(0)i0Et) b3162.3?, d: 1,1970, d01?1809, n1.44741 The above described reaction with (1410) run at 110-700 proceeds rather complexly: the phosphite dehydrochlorinates tho carboxylic esters and the, resulting Me 1-oh1oroaory1ate polymerizes in situ; Et01 is also evolved with formation of (a0),P01.1. The reaction of (iso-PrO),P is similar. A quantitative study of this reaotion ehowed that the aount rec,' (10)2P0H formsd is considerable smaller than the theo- retical, while the amount of evolved RC1 is considerable greater. The expl nation of this feet lie in that at elevated tempi (1N0)2POR reacts with the dihalooarboxylic esters also by the dehydroohlorination route, yielding the polymerio ahloroacrylate and 4:t02(0)(01014:with evolution of Et01, :euch a reaction of (t0) FOR was also tested by heating the ester with Lt0 00Her to 150 when gtBr was evolved and the residue formed an undistillable liquid. The latter on hydrolyeis gave H020CH2P03112. 0f the various possible reaction schemes the most probable Is: (Et0)21,)11 + BrCH C0t .0030) P(OH)- (GE 00 st)Br StBr + Bt0P(0)(01:1)0E: 00 Et, with the originel phosphite reacting in tha enolic form. The same reaction was tried with addn. of (Ma0)2P(0)0NC0z0110:0H2; the latter eater returned unchanged, which was held as a proof of the above scheme, sinoe a reaction scheme: (1040)21(0)11 + (F40) P(0)Clia00zEt + ur3r -+ StEir + (ZtO)P(0')(011)011 00 13t, should have resulted in soma reaotion of the allyl ester with LBr. The resul; II g 915 For ralflginnagnm