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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

DSC Black, RF Crozier and ID Rae

Australian Journal of Chemistry 31(10) 2239 - 2246
Published: 1978

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.

https://doi.org/10.1071/CH9782239

© CSIRO 1978

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