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Synlett 2005(15): 2335-2336  
DOI: 10.1055/s-2005-872670
LETTER
© Georg Thieme Verlag Stuttgart · New York

Formation of New Phosphates from Aldehydes by a DBU-Catalysed Phospha-Brook Rearrangement in a Polar Solvent

Laurent El Kaïm*, Laetitia Gaultier, Laurence Grimaud, Aurélie Dos Santos
Laboratoire Chimie et Procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75739 Paris Cedex 15, France
Fax: +33(1)45525587; e-Mail: laurent.elkaim@ensta.fr;
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Publication History

Received 14 June 2005
Publication Date:
07 September 2005 (online)

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Abstract

Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate.

Key words

Pudovik reaction - dialkylphosphite - phosphate esters - phospha-Brook rearrangement

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