Room Temperature DBN Initiated Phospha-Brook Rearrangement of α-Hydroxyphosphonates to Phosphates

Mahandru-Gill, Muskaan, Iqbal, Aleema, Damai, Margarita, Spiedo, Francesco, Kasonde, Edward Kumbirai, Sykes, Daniel, Devine, Kevin G. and Patel, Bhaven (2022) Room Temperature DBN Initiated Phospha-Brook Rearrangement of α-Hydroxyphosphonates to Phosphates. European Journal of Organic Chemistry. ISSN 1434-193X

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Eur J Org Chem - 2022 - Mahandru-Gill - Room Temperature DBN Initiated Phospha‐Brook Rearrangement of Hydroxyphosphonates.pdf - Accepted Version
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Abstract / Description

A series of substituted aryl phosphate esters have been synthesised from their α hydroxyphosphonates substrates, using DBN (1,5 diazabicyclo(4.3.0)non-5-ene) at room temperature, via a phospha-Brook rearrangement. The aryl-substrate dependence of the rearrangement was explored, and excellent yields of the phosphate esters were achieved irrespective of whether the aryl moiety was activated or unactivated. A plausible mechanism for the rearrangement has been proposed. Based on the low temperature 31P-NMR, the mechanism of the phospha-Brook rearrangement is proposed to take place via an oxaphosphirane intermediate.

Item Type: Article
Uncontrolled Keywords: phospha-Brook rearrangement; Pudovik reaction; α hydroxyphosphonate; phosphate ester; mechanistic studies
Subjects: 500 Natural Sciences and Mathematics > 540 Chemistry & allied sciences
Department: School of Human Sciences
Depositing User: Bhaven Patel
Date Deposited: 21 Oct 2022 08:11
Last Modified: 11 Nov 2022 09:29

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