Next Article in Journal
Cytotoxic Triterpenes from Salacia crassifolia and Metabolite Profiling of Celastraceae Species
Next Article in Special Issue
Continuous Flow Alcoholysis of Dialkyl H-Phosphonates with Aliphatic Alcohols
Previous Article in Journal
Identification of 2′,4′-Dihydroxychalcone as an Antivirulence Agent Targeting HlyU, a Master Virulence Regulator in Vibrio vulnificus
Previous Article in Special Issue
Synergy between Experimental and Theoretical Results of Some Reactions of Annelated 1,3-Azaphospholes
Article Menu
Issue 6 (June) cover image

Export Article

Open AccessFeature PaperReview
Molecules 2018, 23(6), 1493; https://doi.org/10.3390/molecules23061493

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)

Abstract

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
Figures

Scheme 1

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).
SciFeed

Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top