Abstract: Pyridinium salts bearing strong electron-withdrawing groups at positively charged cyclic nitrogen are of great interest because of their incredible synthetic possibilities. Thus the chemistry of N-fluoropyridinium salts is being intensively developed now. Even more interesting in a theoretical aspect are N-fluorodinitromethylpyridinium salts, for fluorodinitromethyl group is close to fluorine atom in its −I effect but in contrast to the latter does not possess +M effect. The synthesis of first representatives of previously unknown class of compounds, N-fluorodinitromethylpyridinium salts (I), was carried out by fluorination of pyridine dinitromethylide with cesium fluoroxysulfate (CEFOX). This reaction is the first example of successful fluorination of ylide structures with CEFOX As expected, salts of this type are of exceptional activity towards nucleophiles. Thus, reactions of I even with low reactive carbanions proceed practically instantly with introduction of C-nucleophiles at position 4. At present we study the chemical transformations of I as the most interesting examples of extremely activated pyridinium salts.

Cite: Semenow V.V. , Gakh A.A.
Synthesis of N-fluorodinitromethylpyridinium salts as first examples of hitherto unknown class of compounds
Journal of Fluorine Chemistry. 1991. V.54. N1-3. 208 . DOI: 10.1016/s0022-1139(00)83718-5 OpenAlex

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≡ OpenAlex:

W1986202355

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