Diverse reactivity of nitrones towards electron deficient acetylenes?

New Journal of Chemistry Pub Date: 2015-05-18 DOI: 10.1039/C5NJ00742A

Abstract

Depending on the nature of N- and C-substituents, nitrones exhibit diverse reactivity towards electron deficient acetylenes. Observed reactions include formal 1,3-dipolar cycloaddition and nucleophilic addition reactions. Possible involvement of zwitterionic intermediates and an unusual 1-aza-Cope rearrangement account for the generation of unexpected 1?:?1 adducts in the reaction of N-arylnitrones.

Graphical abstract: Diverse reactivity of nitrones towards electron deficient acetylenes
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