δ-Alkynyl oximes undergo a concerted 2n + 2π+ 2σ 1,3-azaprotio cyclotransfer (APT) reactiongenerating cyclic N-vinyl nitrones which have been trapped in cycloaddition reactions; MNDO and AM1 calculations and transition-state modelling provide support for the observed greater facility of oxime–alkyne reactions compared to oxime–alkene reactions.
R. Grigg, T. R. Perrior, G. J. Sexton, S. Surendrakumar and T. Suzuki, J. Chem. Soc., Chem. Commun., 1993, 372 DOI: 10.1039/C39930000372
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