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Molecules 2018, 23(6), 1493;

Synthesis and Reactions of α-Hydroxyphosphonates

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
Author to whom correspondence should be addressed.
Received: 8 May 2018 / Revised: 11 June 2018 / Accepted: 16 June 2018 / Published: 20 June 2018
(This article belongs to the Special Issue Organophosphorus Chemistry 2018)


This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids. View Full-Text
Keywords: α-hydroxyphosphonate; Pudovik reaction; O-derivatization; oxidation; substitution; rearrangement; hydrolysis α-hydroxyphosphonate; Pudovik reaction; O-derivatization; oxidation; substitution; rearrangement; hydrolysis

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Rádai, Z.; Keglevich, G. Synthesis and Reactions of α-Hydroxyphosphonates. Molecules 2018, 23, 1493.

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