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.
S. Radhamani, R. Natarajan, P. A. Unnikrishnan, S. Prathapan and J. P. Rappai, New J. Chem., 2015, 39, 5580 DOI: 10.1039/C5NJ00742A
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