A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates-Reference-Cited by-同舟云学术

A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

Published:2020-05-09 Issue:4 Volume:24 Page:465-471
ISSN:1385-2728
Container-title:Current Organic Chemistry
language:en
Short-container-title:COC

Author:

Rádai Zita¹,Szabó Réka¹,Szigetvári Áron²,Kiss Nóra Zsuzsa¹,Mucsi Zoltán¹,Keglevich György¹^ORCID

Affiliation:

1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary

2. Spectroscopy Research Department, Gedeon Richter Plc., 1103 Budapest, Gyömrői út 19-21, Hungary

Abstract

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

Funder

National Research, Development and Innovation Office

Ministry of Human Capacities of Hungary

Hungarian Academy of Sciences

New National Excellence Program of the Ministry of Human Capacities

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

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