Benzoyl peroxide in benzene solution at room temperature converts indoles into indoxyl, oxindole, and dioxindole O-benzoates. The mono-and di-O-benzoates of 1-methylindoxyl, 1,2-dimethylindoxyl, 1,3-dimethyloxindole, and 1-methyldioxindole were prepared from the corresponding V-methylindoles by this convenient one-step procedure in yields of 10-80% depending on the ratio of substrate to reagent. The mechanism is discussed in terms of both homolytic and heterolytic cleavage of the reagent.
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