Intramolecular epoxidation in unsaturated ketones and oxaziridines

A Armstrong, AG Draffan

Index: Armstrong; Draffan Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 21 p. 2861 - 2873

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Citation Number: 4

Abstract

The possibility of intramolecular epoxidation in acyclic unsaturated ketones (via dioxiranes) and oxaziridines (via oxaziridinium species) has been investigated. Treatment of several acyclic unsaturated ketones with Oxone® led to low levels of regio-and stereocontrol, suggesting that background epoxidation by Oxone® dominates. However, treatment of unsaturated oxaziridines with methyl trifluoromethanesulfonate led to intramolecular ...