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Evidence for single electron transfer in the reaction of a lithium enolate with a primary alkyl iodide

✍ Scribed by E.C. Ashby; J.N. Argyropoulos

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 205 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)91134-7

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✦ Synopsis

Evidence for a radical process in the reaction of the lithium enolate of propiophenone with a primary alkyl iodide was obtained by the observation of cyclization of an appropriate radical probe, by the trapping of the radical intermediate and by the comparison of the relative rates of reactions of the probe alkyl iodide with the corresponding bromide and tosylate. The alkylation reaction of enolate anions is an important synthetic reaction whose mechanism is generally recognized to be SN2 in nature.' Nevertheless, radical intermediates have been reported when enolates were allowed to react with ketones, 2,3 esters, 4 nitrobenzene* and 2-chloro-2-nitropropane.5

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