Indolizines. 3. Oxidation products of indolizinols: radicals, ions, and oxidized dimers

DH Wadsworth, CH Weidner, SL Bender…

Index: Wadsworth, Donald H.; Weidner, Charles H.; Bender, Steven L.; Nuttall, Robert H.; Luss, Henry R. Journal of Organic Chemistry, 1989 , vol. 54, # 15 p. 3652 - 3660

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Citation Number: 15

Abstract

'The oxidation products of 1-and 3-indolizinols have been investigated and characterized. A variety of stabilized indolizinols form stable, crystalline free radicals by one-electron oxidations. Both 7-H and 7-CH3 substituted indolizinols, when subjected to exhaustive aerial or benzoquinone oxidation, form the oxidatively coupled 1, l'-or 3, 3'-dioxo-7, 7'- bisindolizines. Two-electron oxidation of indolizinols formed oxoindolizinium ions.