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Issue 0, 1971
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Light-induced and related reactions of quinones. Part VII. Cleavage and isomerisation of some (1-hydroxyalkyl)-1,4-benzoquinones

Abstract

The synthesis is described of 1,4-benzoquinones carrying, severally, the following side-chains: CH(OH)·CH2Ph,CD(OH)·CH2Ph, CMe(OH)·CH2Ph, CH(OH)·CHPh2, CH(OH)·CH2·CH:CH2, and CMe(OH)·CH2·CH:CH2. When irradiated with visible light all the secondary alcohols yield 2,5-dihydroxybenzaldehyde, and all the tertiary alcohols give 2,5-dihydroxyacetophenone, probably via fragmentation of the derived alkoxyl radicals. The tertiary alcohols also yield isomers in which reorganisation of the side-chain has occurred. Mechanisms are suggested.

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J. Chem. Soc. C, 1971, 2244-2252
Article type
Paper

Light-induced and related reactions of quinones. Part VII. Cleavage and isomerisation of some (1-hydroxyalkyl)-1,4-benzoquinones

J. M. Bruce, D. Creed and K. Dawes, J. Chem. Soc. C, 1971, 2244
DOI: 10.1039/J39710002244

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