Tetrahedron p. 173 - 182 (1982)
Update date:2022-08-05
Topics:
Caramella, P
Corsico, A. Coda
Corsaro, A
Del Monte, D.
Albini, F. Marinone
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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