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.clive
ualberta.ca
D. L. J. Clive, J. Wang, J. Org. Chem., 2002, 67, 1192-1198.
DOI: 10.1021/jo010885c
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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
Details
The document discusses the development and application of a novel tin hydride reagent, referred to as stannane 1, designed to facilitate the removal of tin species from products of stannane-mediated radical reactions. This reagent behaves similarly to conventional reagents like Bu3SnH and Ph3SnH in standard free radical reactions but offers the advantage of easier removal of tin-containing byproducts through mild hydrolysis. The hydrolysis process, using either LiOH-water-THF or TsOH-water-THF, converts the byproducts into base-soluble materials that can be easily extracted with aqueous NaHCO3.
The performance of stannane 1 was evaluated across various radical reactions, including reductions of halides and selenides, Barton-McCombie deoxygenation, and enyne cyclization. The effectiveness of the workup procedure in removing tin species was monitored using 1H NMR spectroscopy, demonstrating that the new reagent significantly simplifies product isolation by reducing tin contamination.
The document also provides detailed experimental procedures for the preparation and use of stannane 1, highlighting its stability and efficiency. Overall, the study presents stannane 1 as a valuable tool in organic synthesis, offering a practical solution to the challenge of tin byproduct removal in radical reactions.
Key Words
Tin Hydrides, Barton-McCombie Reaction, Dehalogenations, Cyclopentanes
ID: J42-Y2002-590
