Studies of a novel biomimetic radical spirocyclisation

UP Topiwala, MC Luszniak, DA Whiting

Index: Topiwala, Upendra P.; Luszniak, Mark C.; Whiting, Donald A. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 7 p. 1185 - 1191

Full Text: HTML

Citation Number: 0

Abstract

The mechanism of the radical spirocyclisation 7→ 9 has been investigated. It has been shown by isotopic labelling that the biaryl ether oxygen does not emerge as the carbonyl group oxygen in the product, nor does the latter arise by hydrolysis of an intermediate eg 33 by added water. The mechanism of Scheme 1 path a is proposed, involving oxygen transfer from an aromatic nitro group to carbon in a cyclohexadienyl radical. Radical ...