Zinc(0)–Copper(I) Chloride Promoted Reaction of Methyl Dichlorofluoroacetate with Carbonyl Compounds. A New Efficient Method for the Synthesis of Methyl (Z)-α-Fluoro-α,β-unsaturated Carboxylates
- 5 June 1987
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 16 (6) , 1145-1148
- https://doi.org/10.1246/cl.1987.1145
Abstract
Methyl dichlorofluoroacetate, easily prepared from methyl trichloroacetate and antimony(III) fluoride, underwent the reductive coupling–elimination reaction with carbonyl compounds in the presence of zinc(0), a catalytic amount of copper(I) chloride, acetic anhydride, and molecular sieves to give the corresponding (Z)-α-fluoro-α,β-unsaturated carboxylic acid methyl esters in high yields.This publication has 12 references indexed in Scilit:
- 2,2-Difluoro-3-hydroxyesters by reformatskii reactionTetrahedron Letters, 1984
- Synthesis and properties of 7,7-difluoro derivatives of the 2,6-dioxa[3.1.1]bicycloheptane ring system present in thromboxane A2Journal of the American Chemical Society, 1984
- Preparation of trifluoromethylated allylic alcohols from trifluoroacetaldehyde and organometallic compoundsJournal of Fluorine Chemistry, 1984
- Highly selective re-additions to a masked oxaloacetate. Absolute configurations of fluorocitric acidsJournal of the American Chemical Society, 1981
- New geometric isomers of vitamin A and carotenoids. 6. Fluorinated rhodopsin analogs from 10-fluoro- and 14-fluororetinalJournal of the American Chemical Society, 1978
- Deuterium incorporation via zinc-copper couple reductions of halidesThe Journal of Organic Chemistry, 1974
- Organische Fluorverbindungen, VIII Synthesen und Reaktionen neuer Fluor‐vitamin‐A‐säureesterEuropean Journal of Organic Chemistry, 1965
- Organische Fluorverbindungen, VII. Synthese von 10‐Fluor‐ und 14‐Fluor‐vitamin‐A‐acetatEuropean Journal of Organic Chemistry, 1964
- Organische Fluorverbindungen, IV1). Carbonyl‐FluorolefinierungenEuropean Journal of Organic Chemistry, 1964
- Recherches sur les Composés Organiques Fluorés dans la Série Aliphatique: II. Sur les dérivés des acides mono‐, di‐ et tri‐fluoro‐acétiquesRecueil des Travaux Chimiques des Pays-Bas, 1947