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Published July 1, 1960 | public
Journal Article

Further Evidence for Benzyne as an Intermediate in Nucleophilic Aromatic Substitution Reactions


Some alternatives to the "benzyne" (elimination-addition) mechanism for aminations of non-activated halobenzenes have been disproved by the finding that the amination of iodobenzene-1-^(14)C-2,4,6^(-2)H_3 gives the same extent of ^(14)C rearrangement in the resulting aniline as does iodobenzene-1-^(14)C. The intermediacy of substituted benzynes in non-rearranging aminations of 3-substituted halobenzenes has been confirmed by a study of the hydrogen-deuterium kinetic isotope effect in reactions of 3-bromoanisole-2,4,6-^2H_3.

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© 1960 American Chemical Society. Received November 24, 1959. Supported in part by the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is hereby made to the Donors of this Fund.

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