3-Trimethylsilyl-1-Diethylaminopropyne

Abstract

Corey and Cane¹ have reported that 1-diethylaminopropyne (1) can be lithiated with BuLi in the presence of TMEDA. This Li-ynamine 2 gives readily the 3-silylated derivative 3 upon a treatment with Me₃SiCl. An effort to exdend this to phenylselenenylation of 2 failed. The reaction mixture had a band at 1940 cm⁻¹ in the IR-spectrum probably indicating 1-selenenylation and an allene structure. The reagent 3 can be isolated, but is more conveniently prepared in situ.