The tandem intermolecular Paternò–Büchi reaction: Formation of tetrahydrooxepins

CY Gan, JN Lambert

Index: Gan, Chee Yong; Lambert, John N. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 15 p. 2363 - 2372

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Citation Number: 8

Abstract

The Paternò–Büchi reaction is the [2+ 2] photocycloaddition between carbonyl compounds and electron rich alkenes to generate oxetane products. By the introduction of substituted cyclopropyl rings to the alkene components, the utility of this reaction has been extended to facilitate the synthesis of substituted tetrahydrooxepins. It is proposed that initial addition of oxygen radicals to cyclopropyl enol ethers generates cyclopropylmethyl radicals which, ...