Atherton-Todd phosphorylation

Atherton-Todd phosphorylation of alcohols and phenols (Table 3.22)... 

A two-phase modification of the traditional Atherton-Todd phosphorylation reaction (Table 5.8) is aided by the addition of benzyltriethylammonium chloride [36,37]... 

Atherton-Todd phosphorylation, 353 Azetidinecarboxylic acids, 260 Azidoalkanes, 153 Aziridine, 52 Aziridines, 106 Azirines, 322, 323 Azobenzene, 331, 332, 392 Azobisisobutyionitrile, 224 Azoxybenzene, 331, 332 Azoxybenzenes, 12... 

Phosphorylation of primary alcohols and phenols. Zwierzak has found that the Atherton-Todd phosphorylation can be carried out advantageously under phase-transfer eatalysis. Carbon tetrachloride and 50% aqueous sodium hydroxide serve as the solvent pair tetra-/i-butylammonium bromide or benzyltriethyl-ammonium chloride serve equally well as catalysts. Yields are 35 90% for primary alcohols and phenols low yields are obtained from other alcohols. 

The catalysed two-phase adaptation of the Atherton-Todd procedure is effective for the phosphorylation of primary alcohols and of phenols [6] to produce trialkyl phosphates and dialkyl aryl phosphates. Trialkyl phosphates have also be obtained in high yield (>75%) from the alkylation of preformed tctra-n-butylammonium di-/-butylphosphate [7], Subsequent cleavage of the /-butyl groups provide a simple synthesis of monoalkyl phosphates. 

PTC has been used efficiently for chlorination of dialkylphosphite and subsequent phosphorylation of secondary amines, O-alkylhydroxylamines, alcohols, etc. (Atherton-Todd reaction) via halophilic reaction with carbon tetrachloride ... 

Amino acids were phosphorylated successfully using Atherton-Todd reaction conditions [89,90]. 

It was shown that the phosphorylation of amines by the Atherton-Todd reaction could be carried out conveniently and easily under phase-transfer conditions in the presence of catalytic amounts (about 5 mol %) of triethylbenzylammonium chloride (TEBA) [91]. 

N-phosphorylated proteins and amino acids play important roles in the regulation of enzyme activity and protein biosynthesis [107,108], The Atherton-Todd reaction is used for the convenient synthesis of A-phosphoryldipeptide acids. The dialkyl phosphonate group has been successfully used for direct phosphorylation and for protection of the amine group [109-112],... 

The Atherton-Todd reaction is used for the phosphorylation of poly(A-vinylpyrrolidone-co-vinylamine) [119],... 

General procedure for the phosphorylation of aminoalcohols using Atherton-Todd reaction (ref Zh. Obshch. Khim., 1974, 46, 21). 

The Atherton-Todd reaction is used to introduce a phosphoryl group in amines, but this procedure encounters difficulties when applied to alcohols. Sonication extended its scope to this last type of substrate (Eq. 26). 

A novel phosphorylation method for wyo-inositol derivatives involving application of the Atherton-Todd reaction under solid-liquid phase transfer conditions has been developed. ... 

Atherton, F.R., Openshaw, H.T., and Todd, A.R., Phosphorylation. II. Reaction of dialkyl phosphites with polyhalogen compounds in the presence of bases — method for the phosphorylation of amines, /. Chem. Soc., 660, 1945. 

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