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, 2022 (43). pp. 1-6. ISSN 1099-0690

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Abstract / Description

A series of substituted aryl phosphate esters have been synthesized 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: α-Hydroxyphosphonate; mechanistic studies; Phospha-Brook rearrangement; Phosphate ester; Pudovik reaction
Subjects: 500 Natural Sciences and Mathematics > 540 Chemistry & allied sciences
Department: School of Human Sciences
SWORD Depositor: Pub Router
Depositing User: Pub Router
Date Deposited: 16 Dec 2022 11:10
Last Modified: 16 Dec 2022 11:10


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