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

Douglas A L Otte, Keith Woerpel

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)3906-3909
Number of pages4
JournalOrganic Letters
Volume17
Issue number15
DOIs
StatePublished - Aug 7 2015

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aldehydes
Aldehydes
reagents
electron transfer
Electrons
Bearings (structural)
products
clocks
halides
Clocks
rings

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes. / Otte, Douglas A L; Woerpel, Keith.

In: Organic Letters, Vol. 17, No. 15, 07.08.2015, p. 3906-3909.

Research output: Contribution to journalArticle

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