Synthesis and Radical Reactions of Isomeric Alkenyl Oxaziridines

David St C. Black; Gavin L. Edwards; Sean M. Laaman

doi:10.1055/s-2006-942380

PAPER

Synthesis and Radical Reactions of Isomeric Alkenyl Oxaziridines

David StC. Black*, Gavin L. Edwards*, Sean M. Laaman
School of Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia
Fax: +61(2)93856141; e-Mail: d.black@unsw.edu.au; e-Mail: g.edwards@unsw.edu.au;

Abstract

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Abstract

Several alkenyl oxaziridines were prepared either by photoisomerisation of the precursor nitrones, or by peracid oxidation of the analogous pyrrolines. In each case the oxaziridines were produced as separable mixtures of diastereoisomers, and reasons for the observed stereoselectivity are discussed. Reaction of the oxaziridines with iron(II) sulfate, tributyltin hydride, or copper(I)triphenylphosphine chloride tetramer gave products arising from deoxygenation in many cases; however the trans-isomers also gave products derived from cyclisation of the intermediate aminyl radicals onto the pendant alkenyl chains.

Key words

oxaziridines - radical reactions - nitrones - stereoselectivity - aminyl radicals

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