J Org Chem. 2008 Aug 1;73(15):6018-21. Epub 2008 Jul 2.

[1-(Phenylseleno)alkyl]stannanes-mixed selenium/tin analogs of acetals: preparation from alpha-hydroxystannanes and use for generating selenium-stabilized carbanions.

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Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.

Abstract

Selenium-stabilized carbanions are available by a route that does not involve acid-catalyzed formation of selenoacetals. Aldehydes are converted first into alpha-hydroxystannanes and then into alpha-(phenylseleno)stannanes. Treatment with BuLi affords selenium-stabilized carbanions by preferential Sn/Li exchange.

PMID:: 18593186; [PubMed - indexed for MEDLINE]

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J Org Chem. 2008 Aug 1 ;73(15):6018-21. Epub 2008 Jul 2 .

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