Nitrones and oxaziridines. XXI. Electronic substituent effects in nitrone cycloadditions to highly polarized alkenes

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Abstract
1,3-Dipolar cycloaddition reactions of nitrones-particularly N-(2'- pyridylmethylene)aniline N-oxide-with arylmethylene cyanoacetates exclusively yield 4,4-disubstituted isoxazolidines, identifiable by 1H n.m.r, spectroscopy and isolable in some cases. Comparative kinetic experiments provide evidence for at least non-synchronous addition via a dipolar intermediate or possibly even two-step addition via a discrete zwitterionic intermediate.

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