Nucleophilic substitution at an acetylenic carbon: acetylenic thioethers from haloalkynes and sodium thiolates

GR Ziegler, CA Welch, CE Orzech…

文献索引：Ziegler,G.R. et al. Journal of the American Chemical Society, 1963 , vol. 85, p. 1648 - 1651

全文：HTML全文

被引用次数: 32

摘要

A new type of substrate, the haloalkyne family, has been used in the displacement process. Under mild conditions, eg,-25'in dimethylformamide, nucleophilic displacement on these halides by sodium thiolates has proved to be surprisingly facile. This constitutes a new and convenient route to acetylenic ethers deriving from both aryl and alkyl thiolates. Three interesting diversions from this route are noted: the haloalkyne may enter into oxidation- ...