Acyl polysilanes: new acyl anion equivalents for additions to electron-deficient alkenes

Org Lett. 2009 Jul 2;11(13):2744-7. doi: 10.1021/ol900813z.

Abstract

Silenes, generated through thermolysis of acylpolysilanes, add to alpha,beta-unsaturated esters to form cyclobutanes and silylsubstituted cyclopropanes in moderate yields. Upon Si-C bond oxidation the cyclopropanes are converted directly to 1,4-dicarbonyl compounds, thus demonstrating the formal acyl anion chemistry of acyl polysilanes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Anions
  • Catalysis
  • Cyclobutanes / chemistry
  • Cyclopropanes / chemistry
  • Esters
  • Molecular Structure
  • Oxidation-Reduction
  • Polymers / chemistry*
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Anions
  • Cyclobutanes
  • Cyclopropanes
  • Esters
  • Polymers
  • Silanes