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

Rádai, Zita and Szigetvári, Áron and Kiss, Nóra Zsuzsa and Mucsi, Zoltán and Keglevich, György (2020) A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates. CURRENT ORGANIC CHEMISTRY, 24 (4). pp. 465-471. ISSN 1385-2728

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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.

Item Type:	Article
Subjects:	Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User:	Dr. Nóra Zsuzsa Mireiszné Kiss
Date Deposited:	15 Sep 2020 13:59
Last Modified:	15 Sep 2020 14:09
URI:	http://real.mtak.hu/id/eprint/113294

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