New pyrophosphate analogues: a facile access to N-(O-alkyl-sulfamoyl)phosphoramidic acids via a simple and quantitative reaction of N-(O-alkylsulfamoyl)trimethylphospha-λ5-azene with bromotrimethylsilane and water - Archive ouverte HAL
Article Dans Une Revue Tetrahedron Année : 2004

New pyrophosphate analogues: a facile access to N-(O-alkyl-sulfamoyl)phosphoramidic acids via a simple and quantitative reaction of N-(O-alkylsulfamoyl)trimethylphospha-λ5-azene with bromotrimethylsilane and water

Résumé

A new strategy to prepare pyrophosphate analogues through selective and quantitative cleavage of N-(O-alkylsulfamoyl)trialkylphospha-λ5-azene esters (R–O–SO2–NP(OR′)3) has been developed. Using pure bromotrimethylsilane, N-(O-alkyl-sulfamoyl)tristrimethylsilylphospha-λ5-azenes (R–O–SO2–NP(OSiMe3)3) have been easily obtained as intermediates. N-(O-Alkyl-sulfamoyl)phosphoramidic acids (R–O–SO2–NH–P(O)(OH)2) have been formed quantitatively by hydrolysis of the silylated intermediates.

Domaines

Chimie

Dates et versions

hal-03952341 , version 1 (23-01-2023)

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Citer

Laurent Bonnac, Véronique Barragan-Montero, Jean‐Yves Winum, Jean-Louis Montero. New pyrophosphate analogues: a facile access to N-(O-alkyl-sulfamoyl)phosphoramidic acids via a simple and quantitative reaction of N-(O-alkylsulfamoyl)trimethylphospha-λ5-azene with bromotrimethylsilane and water. Tetrahedron, 2004, 60 (10), pp.2187-2190. ⟨10.1016/j.tet.2004.01.035⟩. ⟨hal-03952341⟩

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