Reaction of arylthioniacycloalkane salts with hydrazine

The reaction between arylthioniacycloalkanes (including sulfonium salts wit h petroleum sulfide moieties) and hydrazine was found to involve the hetero cyclic C-S bond cleavage and hydrazine addition to afford omega-hydrazinoal kylsulfides. The stability of omega-hydrazinoalkylsulfides is determined by the nature of substituents on the aromatic ring and by the presence and th e position of hydroxy groups, which corresponds with the feasibility of for mation of the inner salts betaines. omega-Hydrazinosulfides gradually split out nitrogen and hydrogen; they were stabilized by transformation to the c orresponding oxalates. omega-Hydrazinoalkylarylsulfides were also synthesiz ed by reacting omega-chloroalkylarylsulfides with hydrazine. The obtained r esults may be used for functionalization of petroleum sulfides.