Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Tetrachlorocyclopentadienone O-Oxide, a Facile Oxygen-Atom-Transfer Reagent: The Disproportionation of Cycloalkyldioxyl Radicals
Ian R. DunkinAdam McCluskey
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1998 Volume 71 Issue 6 Pages 1397-1400

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Abstract

Photolysis of tetrachlorodiazocyclopentadiene (1) in oxygen-saturated hydrocarbon solvents results in the transient formation of tetrachlorocyclopentadienone O-oxide (3). This rapidly decomposes, giving rise to products derived from oxidation of the hydrocarbons. Cyclopentane, cyclopentene, cycloheptane, cycloheptene, cycloheptatriene, and indene have been studied. Cycloheptatriene and indene gave only low yields of tractable products, but the others gave the corresponding ketones and secondary alcohols as the major products. Although yields varied considerably, the ketone and alcohol products were always obtained, within experimental error, in a 1 : 1 molar ratio. This observed product ratio supports the disproportionation of cycloalkyldioxyl radicals as a crucial step.

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© 1998 The Chemical Society of Japan
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