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Issue 110, 2014
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Study on the Atherton–Todd reaction mechanism

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Abstract

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)2P(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.

Graphical abstract: Study on the Atherton–Todd reaction mechanism

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Publication details

The article was received on 11 Sep 2014, accepted on 14 Nov 2014 and first published on 14 Nov 2014


Article type: Paper
DOI: 10.1039/C4RA10228B
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RSC Adv., 2014,4, 64733-64736

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    Study on the Atherton–Todd reaction mechanism

    V. Mitova, N. Koseva and K. Troev, RSC Adv., 2014, 4, 64733
    DOI: 10.1039/C4RA10228B

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