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Molecules, Vol. 23, Pages 1493: Synthesis and Reactions of α-Hydroxyphosphonates

Molecules, Vol. 23, Pages 1493: Synthesis and Reactions of α-Hydroxyphosphonates

Molecules doi: 10.3390/molecules23061493

Authors: Zita Rádai György Keglevich

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.

Authors:   Rádai, Zita ; Keglevich, György
Journal:   Molecules
Volume:   23
edition:   6
Year:   2018
Pages:   1493
DOI:   10.3390/molecules23061493
Publication date:   20-Jun-2018
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