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Article << Previous     |     Next >>   Contents Vol 31(10)

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.



Full text doi:10.1071/CH9782239

© CSIRO 1978

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