Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes

Org Lett. 2015 Aug 7;17(15):3906-9. doi: 10.1021/acs.orglett.5b01893. Epub 2015 Jul 27.

Abstract

Addition of allylmagnesium reagents to an aliphatic aldehyde bearing a radical clock gave only addition products and no evidence of ring-opened products that would suggest single-electron-transfer reactions. The analogous Barbier reaction also did not provide evidence for a single-electron-transfer mechanism in the addition step. Other Grignard reagents (methyl-, vinyl-, t-Bu-, and triphenylmethylmagnesium halides) also do not appear to add to an alkyl aldehyde by a single-electron-transfer mechanism.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Electron Transport
  • Indicators and Reagents / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Aldehydes
  • Indicators and Reagents