Markownikoff two-step hydrolithiation of. alpha.-olefins. Transformation of secondary and tertiary alkyl phenyl sulfides to the relevant alkyllithium reagents

CG Screttas, M Micha-Screttas

Index: Screttas,C.G.; Micha-Screttas,M. Journal of Organic Chemistry, 1979 , vol. 44, # 5 p. 713 - 719

Full Text: HTML

Citation Number: 156

Abstract

The transformation of a number of a-olefins to the relevant secondary and tertiary alkyllithium reagents has been accomplished in two steps by first converting them 10 the corresponding alkyl phenyl sulfides throiigh thrir acid-catalyzed reaction with thiophenol, and second by cleaving the sulfides with lithium in tetrahydrofuran (THF). The overall yields ranged from-35 to 80, 6, based on the isolated carboxylic acids after carbonation. ...