Phosphonium Salt Catalyzed Henry Nitroaldol Reactions

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

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 2 , 2004

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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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Article Details

VOLUME: 1
ISSUE: 2
Year: 2004
Page: [137 - 139]
Pages: 3
DOI: 10.2174/1570178043488400
Price: $58

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