Journal of Organic Chemistry p. 3700 - 3703 (1983)
Update date:2022-08-05
Topics:
Nishinaga, Akira
Nakamura, Koichi
Matsuura, Teruo
The title peroxy esters 1, when deprotonated with t-BuOK in DMF to the corresponding phenolate anions, decompose even at -78 deg C to give compounds 2-10.These compounds result undoubtedly from homolysis of the peroxy bond in 1, indicating that the generation of a carbanion at the α-position of the acyl group in peroxy esters (via resonance in the present case) induces ready homolysis of the peroxy bond.The oxidation of 1 with one-electron oxidizing agents gives rise to the corresponding phenoxy radicals, which also induce homolysis of the peroxy bond.
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