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Issue 17, 1970
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The reaction of 2-arenoylaziridines with aldehydes to form oxazolidines

Abstract

2-Arenoylaziridines undergo thermal 1,3-dipolar addition to aromatic aldehydes and chloral via azomethine ylides to give exclusively 4-arenoyloxazolidines. Proof of the orientation of the addition was obtained and the formation of an alternative ring-expansion product was excluded by specific deuterium-labelling experiments. The lack of dependence of the course of the reaction on the stereochemistry of the aziridine, and the observed lack of base-catalysed epimerisation of the oxazolidines, suggested exclusive formation of the oxazolidines via the more stable trans-azomethine ylide and allowed an assignment of the full stereochemistry of the products.

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Article information


J. Chem. Soc. C, 1970, 2383-2394
Article type
Paper

The reaction of 2-arenoylaziridines with aldehydes to form oxazolidines

G. Dallas, J. W. Lown and J. P. Moser, J. Chem. Soc. C, 1970, 2383
DOI: 10.1039/J39700002383

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