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

doi:10.1055/s-2005-872670

LETTER

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;

Abstract

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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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Referenzen

References

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