CARBANIONIC DISPLACEMENT-REACTIONS AT PHOSPHORUS - DIETHYL (2-PYRIDYL)METHYLPHOSPHONATE SYNTHESIS

Authors
CARRAN J WASCHBUSCH R SAVIGNAC P
Citation
J. Carran et al., CARBANIONIC DISPLACEMENT-REACTIONS AT PHOSPHORUS - DIETHYL (2-PYRIDYL)METHYLPHOSPHONATE SYNTHESIS, Phosphorus, sulfur and silicon and the related elements, 123, 1997, pp. 209-218
Citations number
18
Journal title
Phosphorus, sulfur and silicon and the related elements → ACNP
ISSN journal
10426507
Volume
123
Year of publication
1997
Pages
209 - 218
Database
ISI
SICI code
1042-6507(1997)123:<209:CDAP-D>2.0.ZU;2-0
Abstract
We describe the formation and reactions of the alpha-lithiated (2-pyri dyl)methylphosphonate 1. The lithiated alpha-picoline is obtained by m etallation in THF at low temperature with LDA (lithium diisopropylamid e) (2 equiv.). This is then condensed with diethyl chlorophosphate. Th e thus-formed stable carbanion 1 reacts with various electrophiles: H2 O, D2O, TMSCI, RX, and aldehydes in a Wittig-Homer reaction.