Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Generation of Radical Species from Cyclohexane-1,2-dione and the Reaction with Olefins: Preparation of 4,5-Dihydro-7(6H)-benzofuranone Derivatives
Masanori MiuraNoriyoshi AraiKoichi Narasaka
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1998 Volume 71 Issue 6 Pages 1437-1441

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Abstract

Oxidation of cyclohexane-1,2-dione with ammonium hexanitratocerate(IV) (CAN) generates 2,3-dioxocyclohexyl radical, which reacts with electron-rich olefins to afford the corresponding addition products. The adducts thus generated are converted to 4,5-dihydro-7(6H)-benzofuranone by acid treatment. In addition to cyclohexane-1,2-dione, radical species are also generated from cyclopentane-1,2-dione and cycloheptane-1,2-dione.

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© 1998 The Chemical Society of Japan
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