Tetrahedron

The effect of basicity on fluorodenitration reactions using tetramethylammonium salts

DJ Adams, JH Clark, DJ Nightingale

Index: Adams, Dave J.; Clark, James H.; Nightingale, David J. Tetrahedron, 1999 , vol. 55, # 25 p. 7725 - 7738

Full Text: HTML

Citation Number: 18

Abstract

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 HD 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 ...