79158-34-2

Upstream product

• 108054-55-3 diethyl 4-chloro-α-hydroxy-α-methylbenzylphosphonate 

Relevant academic research and scientific papers

Synthesis of α- and γ-Fluoroalkylphosphonates

α-Fluorobenzylphosphonate esters are conventiently made by treating α-hydroxybenzylphosphonate esters with diethylaminosulphur trifluoride.The reaction is not subject to steric impedance and is extended to the α-fluorination of an α-hydroxybenzylphosphine oxide.For α-hydroxyallyl and α-hydroxycinnamylphosphonates, the replacement of the hydroxy group by fluorine proceeds via an SN2' rearrangement to give γ-fluoroalk-1-enylphosphonates exclusively.Dehydration rather than substitution occurs in the case of alcohols of secondary alkylphosphonates.

A Novel Synthesis of α- and γ-Fluoroalkylphosphonates

α-Hydroxybenzylphosphonate esters are efficiently converted into α-fluorobenzylphosphonate esters by diethylaminosulphur trifluoride while the corresponding α-hydroxyallyl- and α-hydroxycinnamylphosphonates undergo fluorination with allylic rearrangement;