Journal of the American Chemical Society

Steric and Stereoelectronic Control of the Mode Selectivity as a Function of Alkene Structure in the Reaction with Dimethyl α-Peroxy Lactone: Cycloadducts and Ene …

W Adam, L Blancafort

Index: Adam, Waldemar; Blancafort, Lluis Journal of the American Chemical Society, 1996 , vol. 118, # 20 p. 4778 - 4787

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Citation Number: 19

Abstract

The oxidation of di-, tri-, and tetrasubstituted alkenes 2 by dimethyl α-peroxy lactone (1) affords the cycloaddition, ene, and epoxidation products 3-6. In the presence of methanol, additionally the trapping products 7 are obtained. The observed dichotomy in the product distribution requires two different paths for this reaction, namely a path via an open, stretched 1, 6 dipole and another path for epoxidation. Both paths arise from an SN2 ...