- Reactions of 1-fluoroalkyl triflates with nucleophiles and bases
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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.
- Dolbier, William R.,Okamoto, Masamune
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- Reductive defluorination of fluoroalkanes
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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.
- Guijarro, David,Martínez, Pedro,Yus, Miguel
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p. 1237 - 1244
(2007/10/03)
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- Facile Transformation of β-D-Ribofuranosyl Purines and Pyrimidines into Their Respective 3'-Deoxy-threo-pentofuranosyl Nucleosides
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Practical syntheses of 3'-deoxy-β-D-threo-pentofuranosyl-uracil, -cytosine, -adenine, and -guanine (3U, C, A, G) from the corresponding ribonucleosides by two one-pot reactions with readily accessible reagents are described.The key reactions are the selective 3'-O-methanesulphonylations of the ribonucleosides, the deoxygenative -hydride shift of the methanesulphonates, and the reduction of in situ generated 3'-deoxy-2'-keto nucleosides therefrom.
- Kawana, Masajiro,Nishikawa, Masahiro,Yamasaki, Noritsugu,Kuzuhara,Hiroyoshi
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p. 1593 - 1596
(2007/10/02)
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- SYNTHESIS OF ALKYL HALIDES UNDER NEUTRAL CONDITIONS
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Primary and secondary alcohols are efficiently converted to the corresponding alkyl halides under neutral conditions.
- Munyemana, Francois,Frisque-Hesbain, Anne-Marie,Devos, Alain,Ghosez, Leon
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p. 3077 - 3080
(2007/10/02)
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- Replecement of the carboxylic acid function with fluorine
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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.
- Patrick, Timothy B.,Johri, Kamalesh K.,White, David H.,Bertrand, William S.,Mokhtar, Rodziah,et al.
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p. 138 - 141
(2007/10/02)
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- Fluorodecarboxylation with Xenon Difluoride
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The reaction between xenon difluoride and aliphatic carboxylic acids causes decarboxylation with replacement of the carboxyl group by fluorine.
- Patrick, Timothy B.,Johri, Kamalesh K.,White, David H.
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p. 4158 - 4159
(2007/10/02)
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