The Lithiated 3-Trimethylsilyl-1-diethylaminopropyne

Abstract

Recently a reaction of 3-timethylsilyl-1-diethylami-nopropyne (1) with carbonyl compounds was reported by this author¹, The reaction gave various silylated amides which were subjectedto further decomposition and oxidation reactions. The known capacity of a silyl group to stabilizea carbanion at the adjacent a-carbon promted me to examine the lithiation of 1. The expected anion formation could be followed either 1-or 3 - (or unselective) attack by electrophiles. In the case the 3-attack predominating it was reasoned that the many reactions of ynamines² and the silyl moiety could then be utilized in further reactions.