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■ Cycloaddition Reactions of Ehtenesulfonic Acid Derivatives with Nitrones

Josette Chanet-Ray, Roger Vessière, and Abdellah Zéroual

*Laboratoire de Chomie Organique 2, Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, Université de Clermont II, B. P. 45, 63170 Aubière, France

Abstract

The reaction of several derivatives of ethenesulfonic acid (CX₂=CX-SO₂ R ; X = H, Br ; R = F, NEt₂) with different nitrones have been investigated. Regiospecific cycloadditions are observed, the reactions lead to 4-substituted isoxarolidines whatever is the nitrone involved. These results confirm Houk’s predictions, according to which the amount of 4-substituted adduct increases with the electrophilic character of the substituted alkenes.