Phosphonium Salt Catalyzed Henry Nitroaldol Reactions
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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Document Type: Review Article
Affiliations: Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1 Canada.
Publication date: 2004-04-01
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