Nicole D Bartolo1, K A Woerpel1. 1. Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
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.
A radical clock system was developed to investigate single-electron transfer (SET) in the reactions of organomagnesium reagents with n class="Chemical">carbonyl compounds. The fluorenylcyclopropyl radical clock was selected because it is the fastest known radical clock. Additions of Grignard reagents to aldehydes or methyl ketonesprovided 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.
Authors: Nicole D Bartolo; Krystyna M Demkiw; Jacquelyne A Read; Elizabeth M Valentín; Yingying Yang; Alexandra M Dillon; Chunhua T Hu; Michael D Ward; K A Woerpel Journal: J Org Chem Date: 2022-02-15 Impact factor: 4.198
Authors: Nicole D Bartolo; Krystyna M Demkiw; Elizabeth M Valentín; Chunhua T Hu; Alya A Arabi; K A Woerpel Journal: J Org Chem Date: 2021-05-12 Impact factor: 4.198