CARBANIONIC DISPLACEMENT REACTIONS AT PHOSPHORUS: DIETHYL (2-PYRIDY L)METHYLPHOSPHONATE SYNTHESIS

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

1 DCPH - Laboratoire Hétéroéléments et Coordination

We describe the formation and reactions of the α-lithiated (2-pyridyl)methylphosphonate 1. The lithiated α-picoline is obtained by metallation in THF at low temperature with LDA (lithium diisopropylamide) (2 equiv.). This is then condensed with diethyl chlorophosphate. The thus-formed stable carbanion 1 reacts with various electrophiles: H 2 O, D 2 O, TMSCl, RX, and aldehydes in a Wittig-Horner reaction.

Mots clés: 2-picoline; LDA; diethyl chlorophosphate; Wittig-Horner reaction

Domaines: Chimie organique

John Carran, Rachel Waschbüsch, Philippe Savignac. CARBANIONIC DISPLACEMENT REACTIONS AT PHOSPHORUS: DIETHYL (2-PYRIDY L)METHYLPHOSPHONATE SYNTHESIS. Phosphorus, Sulfur, and Silicon and the Related Elements, 1997, 123 (1), pp.209-218. ⟨10.1080/10426509708044210⟩. ⟨hal-03166485⟩