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Atherton-Todd Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr027

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Atherton-Todd Reaction. Comprehensive Organic Name Reactions and Reagents. 27:114–118.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The transformation of dialkylphosphite into dialkyl chlorophosphate in the presence of carbon tetrachloride and a base (usually tertiary amine, secondary amine, or primary amine) known as the Atherton–Todd reaction. It has been reported that the formed dialkyl chlorophosphate is too reactive to be isolated which further reacts with alcohol or amine to give phosphate or phosphoramidate. Therefore only a few dialkyl chlorophosphates have been separated so far. Several modifications have been studied and it is found that the original process can be improved effectively by employing an aqueous base and a phase-transfer catalyst. This reaction has wide application in the synthesis of trialkyl phosphates, dialkylphosphorylated amines hydrazines, and hydroxylamines.

Keywords:

  • dialkyl chlorophosphate;
  • dialkylphosphite;
  • phase-transfer catalyst;
  • hydroxylamines