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By L. Mázor

ISBN-10: 0080179037

ISBN-13: 9780080179032

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Example text

Trifluoroacetic acid is not dehalogenated by bases. Only a few aliphatic compounds have a trifluoromethyl group capable of reacting with bases, for example, when the trifluoromethyl group is attached to the carbon a t o m of a carboxylic acid, as in 2-trifluoromethylacrylic acid, its nitrile, amide and ester. Two fluorine atoms situated on the same carbon a t o m also decrease the reactivity of other halogens. Thus, for instance, monofluorotrichloro (bromo, iodo)methane combines readily with bases, but difluorodichloromethane is stable to most chemical and thermal effects.

Fluoroacetophenone can be reduced polarographically; the fluorine is exchanged for hydrogen. Fluorine atoms attached to an aromatic ring can seldom be replaced in nucleophilic reactions. However, when electrophilic groups are also present, they enhance the reactivity of fluorine to a greater extent than other halogens. Diazonium groups are the most active, but nitro groups in ortho or para positions also significantly promote dehalogenation. The presence of several fluorine or chlorine atoms also exerts a weakening effect.

Aromatically b o u n d fluorine can be replaced by hydrogen atoms from a m m o n i a or an amine in nucleophilic substitution reactions: ArF + H N ^ X -*ArN R' + HF X R' However, the reaction takes place only in the presence of electron-releasing substituents on the ring. Aliphatic, cycloaliphatic and even aromatic compounds containing a trifluoromethyl group are very resistant to catalytic hydration, whereas the difluoromethyl group is more reactive. Fluorine directly attached to the benzene ring can be replaced on catalytic hydrogénation, yielding hydrogen fluoride, but there is no reaction with, for example, lithium aluminium hydride.

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Analytical Chemistry of Organic Halogen Compounds by L. Mázor

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