Autoxidation of 2,3-Dialkylindoles

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Abstract
Autoxidation of 2,3-dimethylindole leads to the formation of an oxidized dimer 6a, and 2-methyl-3-ethylindole gives rise to the corresponding product 6c under the same conditions. In contrast, 2-ethyl-3-methylindole resembles 2,3-diethylindole in behavior and forms 2-acetyl-3-methylindole via the 3-hydro-peroxyindolenine, which is an isolable intermediate. Some of the side reactions which occur under autoxidative conditions have been studied, and an attempt has been made to give a satisfactory unified rationalization of our results and those obtained for related autoxidations by numerous other workers.

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