ChemInform Abstract: The Structure and Reactions of (Phenylhydrazonomethylthio)alkanes.

ChemInform Abstract

Phenyliminomethylthioethane (I) and N-methyl-N-phenylhydrazonomethylthioethane (XI) are treated with electrophiles, nucleophiles and oxidative agents. While (XI) is inert towards the halides (II) and alcohols or amines, (I) and (II) form the iminium salts (III). Treatment of (I) with methanol (IV) produces the ethoxyimine (V), trimethyl orthoformate (VI) and the aminoimine (VIIb). Reaction of (I)with the primary amines (VIII) also gives (VII). Oxidation of (I) yields N-phenylformamide (XII), diethyl disulfide (XIII), and compound (XIV). (XI) is subjected to oxidation, forming the sulfoxide (XVI) and/or the sulfone (XV). (I) does not react with thiophenol.