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Room temperature DBN initiated phospha‐Brook rearrangement of α‐hydroxyphosphonates to phosphates

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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

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.

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8027:41586

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8027:41586

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Title:

Room temperature DBN initiated phospha‐Brook rearrangement of α‐hydroxyphosphonates to phosphates

Creators:

Mahandru‐Gill, Muskaan, Iqbal, Aleema, Damai, Margarita, Spiedo, Francesco, Kasonde, Edward Kumbirai, Sykes, Daniel, Devine, Kevin G. and Patel, Bhaven

Identification Number:

https://doi.org/10.1002/ejoc.202201101

Official URL:

https://doi.org/10.1002/ejoc.202201101

Date:

18 November 2022

Subjects:

500 Natural Sciences and Mathematics > 540 Chemistry & allied sciences

Department:

School of Human Sciences

Publisher:

Chemistry Europe ; Wiley-Blackwell