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Phosphonium Salt Catalyzed Henry Nitroaldol Reactions

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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: henry reaction; nitroaldol; organic catalysis; phosphonium salt

Document Type: Review Article

DOI: http://dx.doi.org/10.2174/1570178043488400

Affiliations: Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1 Canada.

Publication date: April 1, 2004

More about this publication?
  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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