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The synthesis of 1‐alkenyl alkyl disulfides, R‐CH=CH‐S‐S‐R′, and di(l‐alkenyl) disulfides, R‐CH=CH‐S‐S‐CH=CH‐R, with R = H or alkyl and R′ = alkyl, is reported. Reaction of 1‐alkenethiolates R‐CH=CH‐SLi(Na), prepared in situ by cleavage of 1‐alkenyl alkyl sulfides with alkali metal in liquid ammonia, with S‐alkyl alkanethiosulfonates, R′‐S‐SO2‐R′ or alkyl thiocyanates, R′‐SCN, affords 1‐alkenyl alkyl disulfides in excellent yields. Reaction of alkenylmagnesium halides, R‐CH=CH‐SMgCl(Br), likewise leads to formation of 1‐alkenyl alkyl disulfides, but yields are moderate. Treatment of l‐ethylthio‐2‐propenylthioethene, CH3‐CH=CH‐S‐CH=CH‐S‐C2H5, with podium amide in liquid ammonia, results in formation of sodium 1‐propenethiolate which reacts with S‐propyl propanethiosulfonate to give propenyl propyl disulfide in good yield. Oxidation in situ of 1‐alkenethiolate anions with iodine affords the corresponding di‐(l‐alkenyl) disulfides.
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Wijers et al. (1969) studied this question.
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