Abstract 1,1‐Bis(alkylthio)‐2‐alkynes RCH2CCCH(SC2H5)2 (I) (with R H or alkyl) can be metallated with alkali metal amides in liquid ammonia or with butyllithium in ether or tetrahydrofuran. Subsequent hydrolysis affords a mixture of 1 and a 1,1‐bis(alkylthio)‐1,2‐alkadiene RCH2CH CC(SC2H5)2 (II); a similar result is obtained starting from II. The ratio of I and II depends on the metallating agent and on the solvent. Sodium ethoxide in liquid ammonia or in ethanol converts I into II completely. Alkylation of metallated I or II with alkyl iodides gives the products RCH2C CC(R′)(SC2H5)2 (IV) and traces of RCH2C(R′)CC(SC2H5)2(V). Reaction with allyl bromide or with chloromethyl ethyl ether leads to the formation of RCH2CCC(CH2CH CH2)(SC2H5)2 (VI) and RCH2CCC(CH2OC2H5)(SC2H5)2 (VII). Acetone reacts to give the carbinol RCH2CCC[C(CH3)2OH](SC2H5)2 (VIII) as the sole product.
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Wildschut et al. (1968) studied this question.
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