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- W1483577264 abstract "The fluorination of hydroxylic groups by reacting their silylethers with phenyltetrafluorophosphorane was investigated over a large range of alcohols belonging to the various usual structural classes, for which widely different reactivities, reaction products, and yields were found. The quantitative, immediate formation of the intermediate monoalkoxytrifluorophosphoranes 5 from the stoichiometric amounts of the reactants was established in almost every case. It generally occurs in very mild conditions and appears to be mainly controlled by steric factors. The subsequent decomposition of 5, as well as redistribution reactions giving the dialkoxydifluorophosphorane 6, and hence the reaction products, are strongly dependent on the class of the alcohol and on the electronic effects of the substituents. The yields in the expected fluoroalkyl compounds range from 15 to 95% for the primary and secondary alcohols. They are generally higher and sometimes near quantitative for tertiary alcohols, β-alkyl substituted primary and secondary alcohols, and when the alcohols are substituted by electro-attracting groups. Transposed fluoroalkyl compounds are formed each time that they correspond to more stable carbocations. Other common side products include alcenes, ethers and the phenylfluorophosphonates 7. When the alcohols are substituted by very strongly electroattracting groups, the alkoxyfluorophosphoranes become too stable and do not give the alkyl fluorides anymore upon decomposition, at 200° or more. A mechanism involving a carbocation as intermediate is proposed." @default.
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- W1483577264 date "1973-01-01" @default.
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- W1483577264 title "Une evaluation du" @default.
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- W1483577264 doi "https://doi.org/10.1016/s0040-4020(01)83214-2" @default.
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