The Journal of Organic Chemistry

Hydrolithiation of. alpha.-olefins by a regiospecific two-step process. Transformation of alkyl phenyl sulfides to alkyllithium reagents

CG Screttas, M Micha-Screttas

Index: Screttas,C.G.; Micha-Screttas,M. Journal of Organic Chemistry, 1978 , vol. 43, # 6 p. 1064 - 1071

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Citation Number: 188

Abstract

The cleavage of primary alkyl phenyl sulfides by lithium naphthalene or lithium dispersion in tetrahydrofuran has been studied. Cleavage takes place in the direction of alkyllithium and lithium thiophenoxide. Preparation of alkyl phenyl sulfides by the anti-Markownikoff addition of thiophenol to cu-olefins and subsequent cleavage by lithium led to the regiospecific addition of the elements of lithium hydride to the olefinic double bond. The overall yields of ...

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