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Electron Transfer Reactions. Reactions of Epoxyketones and Benzoylaziridines With POTASSIUMt

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The results of our studies on the reaction of some epoxyketones and aziridines with potassium in tetrahydrofuran (THF) are presented. Treatment of trans-1,3-diphenyl-2,3-epoxypropan-1-one (1a) with potassium, for example, gives a mixture of acetophenone (9), the chalcone 4a, the dihydrochalcone 14a, the cyclopentene isomers 20a and 21a, the hydroxy acid 10a and benzoic acid 6, whereas the reaction of 1a with potassium, under oxygen saturation, gives a mixture of 4a, 14a, 6, the diketone 17a, the dihydroxycarboxylic acid 7a and the hydroxyfuranone 19a. The reaction of 1a with potassium superoxide, however gives a mixture of 6, 7a and 19a. Similar results are obtained in the reaction of trans-2,3-epoxy-1-phenyl-3-p-tolylpropan-1-one 1b with potassium. The reaction of 7-oxa-2,3-dibenzoylbicyclo[2.2.1]hepta-2,5-diene (22a) with potassium gives a mixture of 6 and o-dibenzoylbenzene (26a), whereas 2,3-dibenzoyl-1,4-dihydro-1,4-diphenyl-1,4-epoxynaphthalene (22b), under analogous conditions, gives a mixture of 6, 1,3-diphenylisobenzofuran (25b), 26a, 2,3-dibenzoyl-1,4-diphenylnaphthalene (26b) and 2-benzoyl-1,4-diphenylnaphthalene (27b). Treatment of the benzoylaziridines 28a-d with potassium gives the stilbenes, 33a,c, the hydroxy amides, 34,a,c,d, and carboxylic acids 6, 11b, whereas the aziridine 35, on treatment with potassium, gives a mixture of the isoquinoline 37 and the phthalimidine 39. Cyclic voltammetric and pulse radiolysis studies have been carried out, in an attempt to characterize the radical anion intermediates involved in these reactions.

Affiliations: 1: Department of Chemistry Indian Insitute of Technology Kanpur 208016, India; 2: Radiation Laboratory University of Notre Dame Notre Dame, IN 46556, USA; 3: Photochemistry Research Unit Regional Research Laboratory Trivandrum 695 019, India


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