Synthesis of α-fluorovinylphosphonates
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1417-1424
- https://doi.org/10.1039/p19860001417
Abstract
A new general synthesis of α-fluorovinylphosphonates is provided by a Wadsworth-Emmons condensation of tetra-alkyl fluoromethylenebisphosphonates (1) with aldehydes and ketones. The reaction shows useful stereoselectivity favouring the less-hindered alkene product (3). Catalytic reduction of these alkenic products generally leads to α-fluoroalkylphosphonates (5), but hydrogenolysis of the carbon–fluorine bond was observed in the case of β-aryl-α-fluorovinylphosphonates. The free phosphonic acids are readily produced by de-esterification using halogenotrimethylsilanes.Keywords
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