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
J. Org. Chem., 2002, 67 (4), pp 1192–1198
DOI: 10.1021/jo010885c
Publication Date (Web): January 31, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, derrick.clive@ualberta.ca

Abstract

Abstract Image

The stannane 1, which is simple to prepare, behaves like the conventional reagents Bu3SnH and Ph3SnH in standard free radical reactions, but with the special characteristic that the tin-containing byproducts are easily and very largely removed by mild hydrolysis (LiOH−water−THF or TsOH−water−THF), which converts them into base-soluble (aqueous NaHCO3) materials. The performance of stannane 1 was evaluated for a range of radical reactions involving halides, selenides, Barton−McCombie deoxygenation, and enyne cyclization. In several cases the effectiveness of the workup procedure in removing tin species was monitored by 1H NMR.

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History

  • Published In Issue February 22, 2002
  • Received August 29, 2001

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