115913-67-2Relevant academic research and scientific papers
Conformational Effects in the Alkali-Metal Reduction of Diaryl Sulfides. 2. Evidence for Episulfide Intermediates
Francisco, Manuel A.,Kurs, Argo,Katritzky, Alan R.,Rasala Danuta
, p. 4821 - 4826 (2007/10/02)
Alkali-metal reduction of a series of diaryl sulfides shows that, if both aryl moieties possess aromatic stabilization energies less than that of the phenyl group ( i.e., able to generate relatively more stable radical anions), the diaryl sulfide forms an episulfide intermediate via regiospecific coupling of the aryl moieties at the stage of a reactive intermediate.The formation of the episulfide intermediate explains why double carbon-sulfur bond cleavage and extrusion of sulfur is observed only in such diaryl sulfides and why there is preference for the formation ofsingle regioisomeric biaryl.
