Synthesis of alkenes via the Peterson reaction

Abstract

The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8)via the Peterson reaction. The α-phenylthiosilanes (2) were prepared from n,n-bis(phenyrthio)acetals (4) by reaction with lithium naphthalenide and chlorotimethylsilane. The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium–N,N,N′,N′- tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide. The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).