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Synlett 2005(15): 2335-2336
DOI: 10.1055/s-2005-872670
DOI: 10.1055/s-2005-872670
LETTER
© Georg Thieme Verlag Stuttgart · New YorkFormation of New Phosphates from Aldehydes by a DBU-Catalysed Phospha-Brook Rearrangement in a Polar Solvent
Further Information
Received
14 June 2005
Publication Date:
07 September 2005 (online)
Publication History
Publication Date:
07 September 2005 (online)
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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