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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Phosphonium Salt Catalyzed Henry Nitroaldol Reactions

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

Volume 1, Issue 2, 2004

Page: [137 - 139] Pages: 3

DOI: 10.2174/1570178043488400

Price: $65


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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