Thermal decomposition of triphenylphosphonium alkyl ester salts

F Castaneda, C Aliaga, C Acuña, P Silva…

Index: Castaneda, Fernando; Aliaga, Christian; Acuna, Cristina; Silva, Paul; Bunton, Clifford A. Phosphorus, Sulfur and Silicon and the Related Elements, 2008 , vol. 183, # 5 p. 1188 - 1208

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Citation Number: 9

Abstract

In thermolyses of molten triphenylphosphonium alkyl ester bromides and chlorides, alkyl= methyl, ethyl, isopropyl, at 130 and 225° C, initial attack of the halide ion on the methyl group gives the methyl halide and ylid 1, Ph 3 P= CH 2, which can be methylated, or is protonated by the phosphonium salt with transylidation giving Ph 3 P+-CH 3 X−, X= Br, Cl. The initial reactions of the ethyl or isopropyl esters are with the halide ion, X−, as a base giving ylid, ...