Issue 5, 2016

Reactivity of aminophosphonic acids. Oxidative dephosphonylation of 1-aminoalkylphosphonic acids by aqueous halogens

Abstract

The reactions of 1-aminoalkylphosphonic acids with bromine–water, chlorine–water and iodine–water were investigated. The formation of phosphoric(V) acid, as a result of a halogen-promoted cleavage of the Cα–P bond, accompanied by nitrogen release, was observed. The dephosphonylation of 1-aminoalkylphosphonic acids was found to occur quantitatively. In the reactions of 1-aminoalkylphosphonic acids with other halogen–water reagents investigated by 31P NMR, scission of the Cα–P bond was also observed, the reaction rates being comparable for bromine and chlorine, but much slower for iodine.

Graphical abstract: Reactivity of aminophosphonic acids. Oxidative dephosphonylation of 1-aminoalkylphosphonic acids by aqueous halogens

Supplementary files

Article information

Article type
Paper
Submitted
10 août 2015
Accepted
28 oct. 2015
First published
28 oct. 2015

Dalton Trans., 2016,45, 2308-2317

Author version available

Reactivity of aminophosphonic acids. Oxidative dephosphonylation of 1-aminoalkylphosphonic acids by aqueous halogens

J. Drabowicz, F. Jordan, M. H. Kudzin, Z. H. Kudzin, C. V. Stevens and P. Urbaniak, Dalton Trans., 2016, 45, 2308 DOI: 10.1039/C5DT03083H

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