Anodic oxidation of monohalogenated phenols

Anodic oxidation of simple o-halogenated phenol derivatives has been investigated. Among the oxidation products, tricyclic ketone 9 was obtained, along with both the corresponding diaryl ethers 3 and 4 and the diaryls 5-8. Additionally, the effect of the alkyl substituent on the oxidation mode was inspected: anodic oxidation of phenols carrying n-propyl or 3-hydroxylpropyl groups 10b and 10c mainly provided the dienone compounds 11 and 15 through two-electron oxidation. (C) 2001 Elsevier Science Ltd. All rights reserved.