Issue 22, 1975

Liquid-phase metal-centred autoxidation of cyclo-octene promoted by rhodium species

Abstract

The rhodium(I)-promoted autoxidation of cyclo-octene, in benzene at 74 °C, gives non-catalytic yields of cyclo-oct-1-en-3-one and cyclo-octanone by a route independent of radical chains and a Wacker cycle. With added styrene, or in NN-dimethylacetamide, the oxidation is catalytic (6 mol of products per mol Rh). The oxidation is interpreted in terms of a rate-limiting metal-centred insertion of oxygen into an allylic carbon–hydrogen bond and subsequent reactions of the resulting cyclo-oct-1-en-3-ol.

Article information

Article type
Paper

J. Chem. Soc., Dalton Trans., 1975, 2440-2443

Liquid-phase metal-centred autoxidation of cyclo-octene promoted by rhodium species

D. Holland and D. J. Milner, J. Chem. Soc., Dalton Trans., 1975, 2440 DOI: 10.1039/DT9750002440

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