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Molecules 2017, 22(7), 1040; doi:10.3390/molecules22071040

On the Reaction of Carbonyl Diphosphonic Acid with Hydroxylamine and O-alkylhydroxylamines: Unexpected Degradation of P-C-P Bridge

1
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 11991 Moscow, Russia
2
School of Pharmacy, Biocenter Kuopio, University of Eastern Finland, P.O. Box 1627, FI-70211 Kuopio, Finland
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 21 May 2017 / Revised: 20 June 2017 / Accepted: 21 June 2017 / Published: 23 June 2017
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1352 KB, uploaded 23 June 2017]   |  

Abstract

Derivatives of methylenediphosphonic acid possess wide spectra of biological activities and are used in enzymology as research tools as well as in practical medicine. Carbonyl diphosphonic acid is a promising starting building block for synthesis of functionally substituted methylenediphosphonates. Investigation of the interaction of carbonyl diphosphonic acid with hydroxylamine clearly demonstrates that it is impossible to isolate oxime within the pH range 2–12, while only cyanophosphonic and phosphoric acids are the products of the fast proceeding Beckmann-like fragmentation. In the case of O-alkylhydroxylamines, corresponding alcohols are found in the reaction mixtures in addition to cyanophosphonic and phosphoric acids. Therefore, two residues of phosphonic acid being attached to a carbonyl group provide new properties to this carbonyl group, making its oximes very unstable. This principally differs carbonyl diphosphonic acid from structurally related phosphonoglyoxalic acid and other α-ketophosphonates. View Full-Text
Keywords: Beckmann fragmentation; carbonyl diphosphonic acid; hydroxylamines Beckmann fragmentation; carbonyl diphosphonic acid; hydroxylamines
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MDPI and ACS Style

Khomich, O.A.; Yanvarev, D.V.; Novikov, R.A.; Kornev, A.B.; Puljulla, E.; Vepsäläinen, J.; Khomutov, A.R.; Kochetkov, S.N. On the Reaction of Carbonyl Diphosphonic Acid with Hydroxylamine and O-alkylhydroxylamines: Unexpected Degradation of P-C-P Bridge. Molecules 2017, 22, 1040.

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