N. Harsági, Z. Radai, N. Z. Kiss, Á. Szigetvári, G. T. Keglevich, “Two step acidic hydrolysis of dialkyl arylphosphonates”, Mendeleev Commun., 2020, Volume 30, Issue 1,Pages <nobr>38

This article is cited in 11 papers

Communications

Two step acidic hydrolysis of dialkyl arylphosphonates

N. Harsági^a, Z. Radai^a, N. Z. Kiss^a, Á. Szigetvári^b, G. T. Keglevich^a

^a Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
^b Spectroscopic Research Division, Gedeon Richter Plc., Budapest, Hungary

Abstract: The HCl-catalyzed hydrolysis of dialkyl arylphosphonates monitored by ³¹P NMR spectroscopy has revealed two consecutive steps characterized by pseudo first order rate constants k₁ and k₂. A reactivity order for the two steps and for the overall two step hydrolysis has been derived depending on the alkoxy and aryl substituents. Besides the A_Ac2 mechanism, the A_Al1 route has been substantiated for the PrⁱO substituent.

Keywords: arylphosphonates, esters, hydrolysis, phosphonic acids, rate constants, reactivity, mechanism..

Language: English

DOI: 10.1016/j.mencom.2020.01.012

	*Supplementary materials:*
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