Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates.

The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants.

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates.

The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, CHOP, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, CHOP, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, CHOP, dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate, CHNOP, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, CHNOP, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, CHClOP, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, CHOP, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C-OH..

Synthesis and Reactions of α-Hydroxyphosphonates.

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.