A High Yield Procedure for 1-Chloro-1-Alkynes

Abstract

Chloroacetylenes constitute a set of compounds with a great variety of synthetic applications.^1,2 Our recent interest in these compounds has developed from the discovery that they produce α-chloroalkenylalanates with lithium aluminumhydride.² It became expedient to find an improved route to their preparation since literature methods do not possess sufficient scope or only afford moderate yields.^2–5 Along with the recent disclosure of Verboom,⁶ we independently found that the reaction of lithium acetylides (1) with N-chlorosuccinimide (2) produces 1-chloro-1-alkynes (3). Our procedure, however, has marked advantages and thus we wish to report our findings.