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

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

Unité Chimie et Procédés

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	D16805ST
Pages (from-to)	2335-2336
Number of pages	2
Journal	Synlett
Issue number	15
DOIs	https://doi.org/10.1055/s-2005-872670
Publication status	Published - 19 Sept 2005
Externally published	Yes

Keywords

Dialkylphosphite
Phospha-Brook rearrangement
Phosphate esters
Pudovik reaction

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10.1055/s-2005-872670

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title = "Formation of new phosphates from aldehydes by a DBU-catalysed phospha-brook rearrangement in a polar solvent",

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.",

keywords = "Dialkylphosphite, Phospha-Brook rearrangement, Phosphate esters, Pudovik reaction",

author = "\{El Ka{\"i}m\}, Laurent and Laetitia Gaultier and Laurence Grimaud and \{Dos Santos\}, Aur{\'e}lie",

year = "2005",

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doi = "10.1055/s-2005-872670",

language = "English",

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T1 - Formation of new phosphates from aldehydes by a DBU-catalysed phospha-brook rearrangement in a polar solvent

AU - El Kaïm, Laurent

AU - Gaultier, Laetitia

AU - Grimaud, Laurence

AU - Dos Santos, Aurélie

PY - 2005/9/19

Y1 - 2005/9/19

N2 - 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.

AB - 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.

KW - Dialkylphosphite

KW - Phospha-Brook rearrangement

KW - Phosphate esters

KW - Pudovik reaction

U2 - 10.1055/s-2005-872670

DO - 10.1055/s-2005-872670

M3 - Article

AN - SCOPUS:25444510404

SN - 0936-5214

SP - 2335

EP - 2336

JO - Synlett

JF - Synlett

IS - 15

M1 - D16805ST

ER -

Formation of new phosphates from aldehydes by a DBU-catalysed phospha-brook rearrangement in a polar solvent

Abstract

Keywords

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