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

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 m...

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Veröffentlicht in:Journal of organic chemistry 2020-06, Vol.85 (12), p.7848-7862
Hauptverfasser: Bartolo, Nicole D, Woerpel, K A
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00481