Tetrahedron

Cumyl phenyl sulfide forms bicumyl instead of cumyllithium upon reductive lithiation. Thiophenoxide as a leaving group in nucleophilic substitution by SET

V Kulkarni, T Cohen

Index: Kulkarni, Vithalanand; Cohen, Theodore Tetrahedron, 1997 , vol. 53, # 36 p. 12089 - 12100

Full Text: HTML

Citation Number: 11

Abstract

Upon reduction with aromatic radical-anions, cumyl phenyl sulfide (1S) yields mainly bicumyl (2) rather than the expected cumyllithium (3), despite a literature report, herein revealed to be in error, that anion 3 is produced. Related examples from the literature are compiled. A suggested mechanism involves a single electron transfer from the generated cumyllithium (3) to the cumyl phenyl sulfide (1 S) leading to thiophenoxide anion and two ...