Abstract α, β-Unsaturated thioethers RCH= CHSR′(R= H, alkyl; R′= alkyl,-CH= CHR,-C≡ CR) and RC≡ CSR′(R= alkyl; R′= alkyl,-C≡ CR) are cleaved by lithium in liquid ammonia to afford alkenethiolates RCH= CHSLi and alkynethiolates RC≡ CSLi, respectively. Subsequent alkylation with R ″Br gives the analogous α, β-unsaturated thioethers RCH= CHSR ″and RC≡ CSR ″in good to excellent yields. A similar result is ...
