A NEW ROUTE TO ALPHA-FLUOROVINYLPHOSPHONATES UTILIZING PETERSON OLEFINATION METHODOLOGY

Authors
WASCHBUSCH R CARRAN J SAVIGNAC P
Citation
R. Waschbusch et al., A NEW ROUTE TO ALPHA-FLUOROVINYLPHOSPHONATES UTILIZING PETERSON OLEFINATION METHODOLOGY, Tetrahedron, 52(45), 1996, pp. 14199-14216
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
45
Year of publication
1996
Pages
14199 - 14216
Database
ISI
SICI code
0040-4020(1996)52:45<14199:ANRTAU>2.0.ZU;2-1
Abstract
Several alpha-fluorovinylphosphonates (6) have been synthesised from t he Peterson olefination reaction applied to both aldehydes and ketones in conjunction with alpha-fluoro-alpha-trimethylsilylmethylphosphonat e (2). The reaction with aldehydes gives mainly the E-isomer whereas r eaction with ketones gives mainly the Z-isomer. We propose a closed tr ansition state to explain the results of our study. Copyright (C) 1996 Elsevier Science Ltd