Abstract

A new route for the synthesis of 2-arylcyclohexanones starting from cyclohexanones was established. This synthetic route involves electrochemical oxidation as the key step and consists of the following four reaction steps: conversion of cyclohexanone ( 1) to the corresponding enol acetate ( 2), anodic oxidation in methanol providing 2-methoxycyclohexanone ( 3), Grignard reaction for introduction of an aryl group affording 1-aryl-2-methoxycyclohexanols ( 6) and acid-catalyzed treatment forming the 2-arylcyclohexanones ( 7). Thus, cyclohexanones bearing a variety of aryl groups at the α-position were prepared in good yields according to this newly developed method. This transformation starting from 1 to 7 may be characterized as a unique arylated 1,2-transposition of the carbonyl group.

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