A new route to α-fluorovinylphosphonates utilizing Peterson olefination methodology

Rachel Waschbüsch (1) , John Carran (1) , Philippe Savignac (1)

1 DCPH - Laboratoire Hétéroéléments et Coordination

Several α-fluorovinylphosphonates (6) have been synthesised from the Peterson olefination reaction applied to both aldehydes and ketones in conjunction with α-lithiated-α-fluoro-αtrimethylsilylmethylphosphonate (2). The reaction with aldehydes gives mainly the E-isomer whereas reaction with ketones gives mainly the Z-isomer. We propose a closed transition state to explain the results of our study.

Domaines: Chimie organique

Rachel Waschbüsch, John Carran, Philippe Savignac. A new route to α-fluorovinylphosphonates utilizing Peterson olefination methodology. Tetrahedron, 1996, 52 (45), pp.14199-14216. ⟨10.1016/0040-4020(96)00859-9⟩. ⟨hal-03166546⟩