Evidence against Single-Electron Transfer in the Additions of Most Organomagnesium Reagents to Carbonyl Compounds

Nicole D. Bartolo, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

A radical clock system was developed to investigate single-electron transfer (SET) in the reactions of organomagnesium reagents with carbonyl compounds. The fluorenylcyclopropyl radical clock was selected because it is the fastest known radical clock. Additions of Grignard reagents to aldehydes or methyl ketones provided no evidence for ring-opened products that would indicate reaction through SET. Additions of some Grignard reagents to aromatic ketones, however, resulted in the formation of ring-opened products, suggesting SET.

Original languageEnglish (US)
Pages (from-to)7848-7862
Number of pages15
JournalJournal of Organic Chemistry
Volume85
Issue number12
DOIs
StatePublished - Jun 19 2020

ASJC Scopus subject areas

  • Organic Chemistry

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