A Convenient Procedure for the Alkylation of Acetylenes

Publisher Website
Google Scholar
Abstract
Internal acetylenes are traditionally prepared by the alkylation of terminal acetylenes in liquid ammonia using sodium amide as the base.1 Although the yields of internal acetylenes prepared in this manner are sometimes good, they are usually in the range of 30–60%. Normant has previously pointed out the efficacy of hexamethylphosphoramide (HMPA) as a solvent for alkylations of sodium acetylide.2 In connection with other synthetic work, we have worked out a facile procedure which allows the synthesis of certain internal acetylenes in high yield. A typical experimental procedure follows

This publication has 1 reference indexed in Scilit: