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

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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.

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