463-18-3Relevant 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.
SYNTHESIS OF ALKYL HALIDES UNDER NEUTRAL CONDITIONS
Munyemana, Francois,Frisque-Hesbain, Anne-Marie,Devos, Alain,Ghosez, Leon
, p. 3077 - 3080 (2007/10/02)
Primary and secondary alcohols are efficiently converted to the corresponding alkyl halides under neutral conditions.
Replecement of the carboxylic acid function with fluorine
Patrick, Timothy B.,Johri, Kamalesh K.,White, David H.,Bertrand, William S.,Mokhtar, Rodziah,et al.
, p. 138 - 141 (2007/10/02)
Replacement of a carbonyl function by fluorine, fluorodecarboxylation, is a new process that can be accomplished by the reaction of alkanoic acids with xenon difluoride.Primary, tertiary, and benzylic acids perform best in the reaction, which is conducted at room temperature in methylene chloride or chloroform solution.A reaction mechanism is proposed in which the acid is initially converted to a fluoroxenon ester, RCO2XeF.The esters of the primary and secondary acids react by nucleophilic displacement by fluoride, as evidenced by incorporation of 18F- and no reactions common to free radicals or carbocations.The esters of the tertiary and benzylic acids react by converting to free radicals that can be further oxidized to carbocations.Thus incorporation of 18F- and racemization are observed with α-methoxy-α-trifluoromethylphenylacetic acid.Hydroxyl and amino functions inhibit the reaction.Aromatic and vinylic acids do not react.
