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

J Org Chem. 2008 Aug 1;73(15):6018-21. doi: 10.1021/jo8004292. Epub 2008 Jul 2.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Aldehydes / chemistry
  • Alkylation
  • Carbamates / chemistry*
  • Hydroxylation
  • Molecular Structure
  • Oxides / chemistry
  • Propanols / chemistry
  • Selenium / chemistry*
  • Selenium Compounds / chemical synthesis*
  • Selenium Compounds / chemistry
  • Tin / chemistry*
  • Tin Compounds / chemical synthesis*
  • Tin Compounds / chemistry

Substances

  • Acetals
  • Aldehydes
  • Carbamates
  • Oxides
  • Propanols
  • Selenium Compounds
  • Tin Compounds
  • stannane
  • allyl alcohol
  • Tin
  • Selenium