Chemistry of acetylenic ethers. LI: Introduction of alkylthio groups into acetylenic compounds and into other compounds with reactive hydrogen atoms by means of disulphides

Acetylenic compounds RC ≡ CH can be converted into acetylenic thioethers by treatment of the sodium or lithium alkynide with diethyl disulphide in liquid ammonia. This constitutes the easiest route to 1‐ethylthio‐1‐alkynes I. Other compounds with “acidic” CH3, CH2 or CH groups can likewise be alkylthiolated; generally the product containing two geminal ethylthio groups is formed in excess.