- Indolizines. 3. Oxidation Products of Indolizinols: Radicals, Ions, and Oxidized Dimers
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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 the exhaustive aerial or benzoquinone oxidation, from the oxidatively coupled 1,1'- or 3,3'-dioxo-7,7'-bisindolizines.Two-electron oxidation of indolizinols formed oxoindolizinium ions.
- Wadsworth, Donald H.,Weidner, Charles H.,Bender, Steven L.,Nuttall, Robert H.,Luss, Henry R.
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p. 3652 - 3660
(2007/10/02)
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- Enamines from Iodine Oxidation of Trialkylamines. 1. Electrophilic Capture by Cationic Heterocyclic Rings
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Simple enamines derived from acetaldehyde, acetone, and propionaldehyde were generated in situ by iodine oxidation of triethylamine, N,N-diisopropylmethylamine, and tri-n-propylamine, respectively.The enamines were captured by a variety of cationic substrates including trityl, indolizinium, dithiolium, pyrylium, thiapyrylium, selenapyrylium, and tellapyrylium cations.The use of a second equivalent of iodine (or excess) oxidized the initial products of enamine capture to various iminium dyes.These dyes were easily hydrolyzed to heterocyclylidene aldehydes and ketones.Cyclic amines such as N-methylpyrrolidine gave enamines derived from ring oxidation. 2-Cyano-N,N-dimethylethylamine generated a cyano-substituted enamine under the reaction conditions.
- Wadsworth, Donald H.,Detty, Michael R.,Murray, Bruce J.,Weidner, Charles H.,Haley, Neil F.
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p. 2676 - 2681
(2007/10/02)
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