A Tin Hydride Designed To Facilitate Removal of Tin Species from Products of Stannane-Mediated Radical Reactions

Derrick L. J. Clive* and Jian Wang

*Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2, Email: derrick.cliveualberta.ca

D. L. J. Clive, J. Wang, J. Org. Chem., 2002, 67, 1192-1198.

DOI: 10.1021/jo0158534

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see article for more reactions

Abstract

A stannane, which is simple to prepare, was successfully used in standard radical reactions as replacement of Bu₃SnH and Ph₃SnH. The tin-containing byproducts are removed by mild hydrolysis and extraction with aqueous NaHCO₃. The performance of this new reagent was tested for reactions involving halides, selenides, Barton-McCombie deoxygenation and enyne cyclization.

preparation of stannane

formation of water soluble byproducts

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Key Words

Tin Hydrides, Barton-McCombie Reaction, Dehalogenations, Cyclopentanes

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ID: J42-Y2002-590