- Fluorocarbon Derivatives of Nitrogen. Part 8. Reactions Between Heteroaromatic N-Imines (N-Iminopyridinium and N-Iminoquinolinium Ylide) and Perfluoropropene, 2H-Pentafluoropropene, Perfluorobut-2-ene, Perfluoro-(2-methylpent-2-ene), Perfluorobut-2-yne, and Perfluoropyridine: Synthesis..
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N-Iminopyridinium ylide reacts with perfluoropropene (or 2H-pentafluoropropene) and perfluorobut-2-ene (or perfluorobut-2-yne) to provide 2-fluoro-3-(trifluoromethyl)pyrazolopyridine and 2,3-bis(trifluoromethyl)pyrazolopyridine, respectively; oxidation of these products with aqueous potassium permanganate gives the corresponding pyrazolecarboxylic acids.Perfluoro-(2-methylpent-2-ene) is attacked by N-iminopyridinium ylide to produce 2-(pentafluoroethyl)-3,3-bis(trifluoromethyl)-3,3a-dihydropyrazolopyridine, which can be converted via thermal treatment with tetracyanoethylene into a mixture of 2-(pentafluoroethyl)-3-(trifluoromethyl)pyrazolopyridine and 5-(dicyanomethylene)-2-(pentafluoroethyl)-3,3-bis(trifluoromethyl)-3,5-dihydropyrazolopyridine.N-Iminoquinolinium ylide reacts with perfluoropropene, perfluorobut-2-ene, and perfluoropyridine in hot dimethylformamide in the presence of potassium carbonate to yield 2-fluoro-3-(trifluoromethyl)pyrazoloquinoline, 2,3-bis(trifluoromethyl)pyrazoloquinoline, and N-(tetrafluoro-4-pyridyl)iminoquinolinium ylide, respectively.
- Banks, Ronald E.,Hitchen, Stephen M.
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p. 1593 - 1600
(2007/10/02)
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