Tetrahedron p. 189 - 198 (1984)
Update date:2022-08-12
Topics:
Appelman, Evan H.
Basile, Louis J.
Hayatsu, Ryoichi
The effects of the acid catalysts HF, H2SO4, BF3, CF3SO3H, FSO3H, and SbF5*FSO3H on the reactions of CsSO4F with toluene, nitrobenzene and naphthalene in CH3CN have been studied.The catalysts in general accelerate reaction and enhance yields of ring-fluorinated products.Efficacity roughly parallels H0 of the acids, though H2SO4 is more effective than stronger acids for fluorination of naphthalene.Combined room temperature yields of fluorine-substituted products are as much as 45-50 percent for toluene and naphthalene and up to 30 percent for nitrobenzene.The predominant products are o-fluorotoluene, 1-fluoronaphthalene, and m-fluoronitrobenzene.With naphthalene the isomer selectivity is considerably less than in the absence of catalyst.Low yields ( =< 10 percent) of monomeric oxygenated products are obtained, along with considerable oxygen- and fluorine-containing dimers and higher polymers.The results are interpreted in terms of acid-catalyzed electrophilic fluorination or oxygenation, followed by further fluorination and/or freeradical-induced oxidative coupling of the oxygenated products.
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