Journal
RSC ADVANCES
Volume 4, Issue 110, Pages 64733-64736Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ra10228b
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Funding
- National Science Fund of Bulgaria (National Center for Advanced Materials (UNION) Module 2 New materials in medicine and pharmacy [DCVP 02-2/2009]
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A new mechanism of the Atherton-Todd reaction is discussed. The first step of the reaction between diesters of H-phosphonic acid and carbon tetrachloride in the presence of a base, commonly triethylamine, is a salt formation between carbon tetrachloride and the base [amine.Cl]+CCl3-. The trichloromethanide anion [CCl3-] deprotonates dialkyl H-phosphonate to form chloroform and dialkyl phosphonate anion [(RO)(2)P(O)](-). The latter anion reacts with the chlorine cation to furnish dialkyl chlorophosphate. Based on these findings the reaction has been applied for the oxidation of poly(alkylene H-phosphonate)s to the corresponding poly(alkylene chlorophosphate)s via the Atherton-Todd reaction.
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