PHOSPHONIC SYSTEMS .16. REACTION OF METHY L PROPENYLPHOSPHONATE CARBANION WITH KETONES - REVERSAL OF THE NUCLEOPHILE-ELECTROPHILE FUNCTION

Authors
MULLER EL MODRO AM MODRO TA
Citation
El. Muller et al., PHOSPHONIC SYSTEMS .16. REACTION OF METHY L PROPENYLPHOSPHONATE CARBANION WITH KETONES - REVERSAL OF THE NUCLEOPHILE-ELECTROPHILE FUNCTION, Bulletin de la Societe chimique de France, 131(9), 1994, pp. 959-964
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
131
Issue
9
Year of publication
1994
Pages
959 - 964
Database
ISI
SICI code
0037-8968(1994)131:9<959:PS.ROM>2.0.ZU;2-I
Abstract
Lithiated diethyl prop-2-enylphosphonate (allylic phosphonate anion) a dds to ketones via the gamma-carbon (kinetic product) or the gamma-car bon (thermodynamic product) of the allylic system. For enolizable keto nes, the major reaction under thermodynamic conditions is however not the formation of a gamma-adduct, but the deprotonation of a ketone by the allylic phosphonate carbanion, followed by the conjugated addition of the enolate ion to the vinylic phosphonate formed via the prototro pic isomerization of the starting allylic ester.