Conjugated nitroalkenes in cycloaddition reactions 18*. Regio- and stereoselectivity of (2+3) cycloaddition reactions between gem-chloronitroethene and (Z)-C,N-diarylnitrones

Abstract

(2+3) Сycloadditions of gem-chloronitroethene to diarylnitrones proceed regiospecifically and lead to stereoisomeric mixtures of 3,4-cis- and 3,4-trans-2,3-diaryl-4-chloro-4-nitroisoxazolidines. The interpretation of the regiospecificity of the reaction based on the theory of reactivity indices shows that its course is determined by an attack of the nucleophilic center at the nitrone oxygen atom to the electrophilic center at the gem-chloronitroethene.