Selectivity in cycloadditions-IX: Cycloadditions of nitrile oxides to indoles. Reactivity and regiochemistry |
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| Authors: | P Caramella A Coda Corsico A Corsaro D Del Monte F Marinone Albini |
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| Institution: | Department of Chemistry, University of Catania, Viale A. Doria 8, I-95125 Catania and Institute of Organic Chemistry, University of Pavia, Viale Taramelli 10, I-27100 Pavia, Italy |
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| Abstract: | Cycloadditions of benzonitrile oxide and mesitonitrile oxide to N-methylindole and indole yield the acid sensitive cycloadducts 1 a-d with high regioselectivity. With N-carbethoxyindole the stable cycloadducts 1 e,f and minor amounts of the regioisomeric 2 e,f are isolated. The electron withdrawing substituent reduces both the regioselectivity and the reactivity of the cycloadditions.Frontier orbital considerations, based on MINDO/3 calculations, allow elucidation of the observed changes in reactivity and regiochemistry. |
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