Studies on 1, 3-Dithiolium Cations. II. Reactions of 4-Phenyl Derivatives with Nucleophilic Reagents

Abstract

Nucleophilic reagents attacked exclusively to C-2 position of 4-phenyl-1, 3-dithiolium cation derivatives and the corresponding 1, 3-dithioles were obtained in good yields. Thus, 2-amino-, 2-aminothiocarbonylthio-, 2-phenylthio-1, 3-dithioles were yielded. LiAIH4 reduction furnished 1, 3-dithiole and hydride abstraction gave original cation. 1, 3-Dithiolium cation acted as a Bronsted acid and conjugate base carbinol was isolated. Similarly, covalent 2-alkoxy compounds were easily obtained and regenerated cation by the action of acid. Grignard reaction toward cation opened the new routes to 2-substituted 1, 3-dithiolium cations.