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The regiochemistry of trapped radical anion-radical cation pairs from aryl substituted phthalimides

✍ Scribed by Paul H. Mazzocchi; Frederick Khachik

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
203 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of 4-substituted N-methyl phthalimides was irradiated in the presence of 2,3-dimethyl-Z-butene in methanol and the product distributions of the trapped radical anionradical cation analyzed on the basis of substituent effects on the radical anion. Irradiation of N-methylphthalimide in the presence of alkenes results in two apparently competing processes. from a strong donor (OCH3) to a strong acceptor (C02Me). Clearly these results are in accord with predictions from electrochemical studies and are consistent with the intermediacy of a ground state phthalimide radical anion-alkene radical cation in this reaction.

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