Tetrahedron

Peroxydicarbonate-mediated oxidation of N-(ortho-aryloxyphenyl) and N-(ortho-arylaminophenyl) aldimines

R Leardini, H McNab, D Nanni

Index: Leardini, Rino; McNab, Hamish; Nanni, Daniele Tetrahedron, 1995 , vol. 51, # 44 p. 12143 - 12158

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Citation Number: 28

Abstract

Imidoyl radicals 5, obtained from imines 1 by hydrogen abstraction with di-iso-propyl peroxydicarbonate (DPDC), give dibenzoxazepines through 7-membered ring closure. A competitive 6-membered cyclisation leads to intermediate spirocyclohexadienyl radicals that rearrange to aryloxy radicals; this process entails a novel 1, 5-aryl radical translocation from an oxygen to a carbon atom and leads to benzophenones, benzoxazoles, and biphenyls. ...