Phosphonium Salt Catalyzed Henry Nitroaldol Reactions

J.      McNulty; J.      Dyck; V.      Larichev; A.      Capretta; A.   J.   Robertson

doi:10.2174/1570178043488400

Abstract

Trihexyl(tetradecyl)phoshonium decanoate was shown to be an effective promoter for the Henry nitroaldol reaction of nitromethane with aromatic aldehydes. A mechanism is proposed involving Lewis acid activation of the carbonyl group proceeding through a trigonal-bipyramidal intermediate. Evidence in accord with the postulated pathway as opposed to a base or phase transfer-mediated route involving proton transfer from the nitroalkane is presented.

Keywords: nitroaldol, henry reaction, phosphonium salt, organic catalysis

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Letters in Organic Chemistry

Title: Phosphonium Salt Catalyzed Henry Nitroaldol Reactions

Volume: 1 Issue: 2

Author(s): J. McNulty, J. Dyck, V. Larichev, A. Capretta and A. J. Robertson

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Keywords: nitroaldol, henry reaction, phosphonium salt, organic catalysis

Abstract: Trihexyl(tetradecyl)phoshonium decanoate was shown to be an effective promoter for the Henry nitroaldol reaction of nitromethane with aromatic aldehydes. A mechanism is proposed involving Lewis acid activation of the carbonyl group proceeding through a trigonal-bipyramidal intermediate. Evidence in accord with the postulated pathway as opposed to a base or phase transfer-mediated route involving proton transfer from the nitroalkane is presented.

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McNulty J., Dyck J., Larichev V., Capretta A. and Robertson J. A., Phosphonium Salt Catalyzed Henry Nitroaldol Reactions, Letters in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570178043488400