Diaryl Sulfide Cleavage by Sodium Sulfide in Dipolar Aprotic Solvents

Article abstract of DOI:10.1021/jo00163a013

The interaction of sodium sulfide with diaryl sulfides that possess electron-withdrawing substituents (e. g., cyano or nitro) on the aromatic rings results in cleavage of the thioether and the formation of sodium aryl sulfides in dipolar aprotic solvents.Exchange reactions between these diaryl sulfides and sodium aryl sulfides are also observed in dipolar aprotic solvents.The cleavage and exchange reactions were employed to prepare mixed diaryl or alkyl aryl sulfides from symmetrical diaryl sulfides.