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The effect of basicity on fluorodenitration reactions using tetramethylammonium salts

✍ Scribed by Dave J Adams; James H Clark; David J Nightingale

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 638 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00409-3

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✦ Synopsis

The fluorodenitration of several nitroaromatics with tetramethylammonium salts has been found to be dependent on the basicity of the fluorinating species. Tetramethylammonium fluoride is highly basic and is capable of inducing H-D exchange in 1,3-dinitrobenzene, as well as deprotonating N,N-dimethylacetamide.

Reaction of the fluoride with phthalic anhydride forms the bifluoride in situ. Tetramethylammonium bifluoride gives higher yields of the required fluoroaromatic, but slower reaction rates than the corresponding fluoride.

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