The effect of basicity on fluorodenitration reactions using tetramethylammonium salts

Adams, D. J. , Clark, J. H. and Nightingale, D. J. (1999) The effect of basicity on fluorodenitration reactions using tetramethylammonium salts. Tetrahedron, 55(25), pp. 7725-7738. (doi:10.1016/S0040-4020(99)00409-3)

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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 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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Adams, Dave
Authors: Adams, D. J., Clark, J. H., and Nightingale, D. J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier
ISSN:0040-4020
ISSN (Online):1464-5416
Published Online:19 July 1999

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