62127-42-8Relevant articles and documents
Reactions of 1-fluoroalkyl triflates with nucleophiles and bases
Dolbier, William R.,Okamoto, Masamune
, p. 33 - 41 (2015/03/04)
A series of 1-fluoroalkyl triflates are prepared, isolated and characterized. Their reactions with a large variety of nucleophiles are described. From these reactions are obtained 1-fluoroalkyl nitriles, azides, formates, acetates, ethers, phenylthio ethers, triphenylphosphonium salts, benztriazoles, benzimidazoles, xanthates, iodides, bromides and chlorides, most in excellent yield.
Preparation of 1,1-difluoroalkanes from aldehydes via 1,1-bistriflates: Advantageous use of HF-Lewis base reagents
Dolbier, William R.,Okamoto, Masamune
, p. 96 - 100 (2015/03/05)
Alkane-1,1-bistriflates, prepared in excellent yields by reaction of aldehydes with triflic anhydride, are converted to their respective 1,1-difluoroalkanes in good to excellent yield through reaction with fluorinating agent, triethylaminetrishydrofluorid
Stereocontrolled generation of nucleophilic (Z)- or (E)-α- fluoroalkenylchromium reagents via carbon-fluorine bond activation: Highly stereoselective synthesis of (E)- or (Z)-β-fluoroallylic alcohols
Nihei, Takashi,Yokotani, Saya,Ishihara, Takashi,Konno, Tsutomu
supporting information, p. 1543 - 1545 (2014/02/14)
Highly nucleophilic (Z)- or (E)-α-fluoroalkenylchromium species could be generated in a stereoselective manner via C-F bond activation of CBrF 2-containing molecules, and they reacted smoothly with various aldehydes to give (E)- or (Z)-β-fluoroallylic alcohol derivatives in high yields, respectively. The Royal Society of Chemistry.
Impact of fluorine substituents on the rates of nucleophilic aliphatic substitution and β-elimination
Martinez, Henry,Rebeyrol, Adele,Nelms, Taylor B.,Dolbier Jr., William R.
experimental part, p. 167 - 175 (2012/03/27)
A measure of the quantitative effect of proximate fluorine substituents on the rates of SN2 and E2 reactions has been obtained through a study mainly of reactions of fluorinated n-alkyl bromides with weak base, strong nucleophile azide ion and strong base/nucleophile methoxide ion in the protic solvent methanol and the aprotic solvent, DMSO. The order of reactivity for SN2 reactions of azide in methanol at 50 °C was found to be: n-alkyl-Br > n-alkyl-CHFBr > n-perfluoroalkyl-CH2CH 2Br n-perfluoroalkyl-CH2Br > n-alkyl-CF2Br. Approximate relative rates of reaction were: 1, 0.20, 0.12, 1 × 10 -4, -5. The order of reactivity for E2 reactions was found to be: n-perfluoroalkyl-CH2CH2Br n-alkyl-CF2Br > n-alkyl-CHFBr > n-alkyl-Br. The approximate relative rates for reaction of methoxide in methanol at 50 °C were: 1100, 4.4, 1.9, 1.
Reductive defluorination of fluoroalkanes
Guijarro, David,Martínez, Pedro,Yus, Miguel
, p. 1237 - 1244 (2007/10/03)
The reaction of an excess of lithium powder and a catalytic amount of DTBB with primary, secondary and tertiary fluoroalkanes in the presence of a substoichiometric amount of 1,2-bis(trimethylsilyl)benzene 1 afforded the corresponding alkanes resulting from a fluorine-hydrogen exchange. The method could be extended to non-geminal difluorides. The effect of the disilylated compound in the naphthalene-catalysed lithiation of fluorobenzene and benzyl fluoride was also studied.