Synthesis of alkylthio benzene derivatives via simultaneous diazotization and nucleophilic displacement

Abstract

Alkylthio benzene derivatives were effectively synthesized by simultaneous diazotization of aromatic amines and nucleophilic displacement. The method is fairly general and proceeds in moderate yields. Product yields were comparable regardless of steric hindrance of the thiol or of the functional group present in the starting material. The newly developed procedure allowed for the incorporation of a tertiary alkylthio group, which cannot be easily introduced otherwise. The products were characterized by 1H NMR and 13C NMR.

Keywords

• Diazo compounds
• Thiols
• Nucleophilic aromatic substitution
• Thioethers
• Alkylthio benzene