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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 123, 1997 - Issue 1
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Original Articles

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

John Carran Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653, DCPH, Ecole Polytechnique, 91128, Palaiseau Cedex, France Phone: (+33) 01 69 33 45 79 Fax: (+33) 01 69 33 45 79
,
Rachel Waschbüsch Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653, DCPH, Ecole Polytechnique, 91128, Palaiseau Cedex, France Phone: (+33) 01 69 33 45 79 Fax: (+33) 01 69 33 45 79
&
Philippe Savignac Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653, DCPH, Ecole Polytechnique, 91128, Palaiseau Cedex, France Phone: (+33) 01 69 33 45 79 Fax: (+33) 01 69 33 45 79
Pages 209-218 | Received 10 Dec 1996, Accepted 12 Feb 1997, Published online: 04 Oct 2006
 
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Abstract

We describe the formation and reactions of the α-lithiated (2-pyridyl)methylphosphonate 1. The lihated 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: H2O. D2O, TMSCI, RX, and aldehydes in a Wittig-Homer reaction.

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