20397-58-4Relevant articles and documents
Acylation of Fluorocarbethoxy-Substituted Ylids: A Simple and General Route to α-Fluoro β-Keto Esters
Thenappan, Alagappan,Burton, Donald J.
, p. 273 - 277 (1991)
(Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salt 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields.The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides.Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt.Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts.However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with RFCOCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives RFCOCFHCOOEt.
ONE-POT SYNTHESIS OF α-FLUORO-α,β-UNSATURATED ESTERS FROM CHLOROMALONIC ESTER AND CARBONYL COMPOUNDS USING "SPRAY-DRIED" POTASSIUM FLUORIDE
Kitazume, Tomoya,Ishikawa, Nobuo
, p. 1259 - 1260 (1981)
α-Fluoro-α,β-unsaturated esters were prepared by one-pot reaction between aldehydes or ketones and diethyl chloromalonate in the "spray-dried" potassium fluoride-sulfolane system.
Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles
Nihei, Takashi,Kubo, Yusuke,Ishihara, Takashi,Konno, Tsutomu
, p. 110 - 121 (2015/03/04)
Treatment of β-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 °C for 0.25 to 24 h gave γ-products in a highly regioselective manner. Thus obtained γ-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields.
Microwave-assisted one-pot synthesis of α-fluoro-α,β- unsaturated esters under solvent-free conditions
Ren, Aishan,Yang, Xiongjun,Hong, Jing,Yu, Xiaochun
experimental part, p. 2376 - 2378 (2009/05/27)
A microwave-assisted approach for the synthesis of α-fluoro-α, β-unsaturated esters from ethyl bromofluoroacetate, aldehydes, and triphenylphosphine in the presence of Zn-Cu under solvent-free conditions was achieved. The reaction was accomplished within
