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Evidence for single electron transfer in the reactions of organometallic compounds with 2,3,3-trimethyl-2-butyl peroxybenzoate

✍ Scribed by W.F. Hendrickson Jr.; W.D. MacDonald; S.T. Howard; E.J. Coligado

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 272 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98586-1

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✦ Synopsis

Utilization of a triptoxy radical probe in the with 2,3,3-trimethyl-2-butyl peroxybenzoate indicates reaction decreases in the order B-BuLi>B-BuMgCl>PhMgBr. reactions of organometallic compounds that the radical character of the Peroxides may react with nucleophiles either by nucleophilic displacement (SN2)l or single electron transfer (SET) mechanisms,2 and these reactions thus provide a rich area in which to study the dichotomy between these two mechanisms. Many of the peroxide SET reactions reported recently have enployed electron donors such as polynuclear aromatics,2arb dimethoxybenzenes,2dre and anispinacolone, 2c which are relatively weak nucleophiles. In these Cases SN2 WUid not be eXpeCted to Con&&e with sm. The

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