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Communication | Special issue | Vol 7, No. 2, 1977, pp.871-876
Published online, 1st January, 1970
DOI: 10.3987/S-1977-02-0871
1,3-Dipolar Cycloaddition Reaction of Aromatic N-Oxide with Hexafluorobutyne-2

Yoshiro Kobayashi,* Itsumaro Kumadaki, and Shomi Fujino

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Reaction of quinoline and isoquinoline N-oxides with hexafluorobutyne-2 (1) was examined. The former gave 2-(2-quinolyl)-3-trifluoroacetoxy-1,1,1,4,4,4-hexafluoro-2-butene, quinolinium trifluoromethyltrifluoroacetylmethylide, 2-(2,2,2-trifluoroethy1)quinoline and 2,3-bis(trifluoromethyl)furo[3,2-b]quinoline. The latter gave isoquinolinium trifluoroacetylfluorocarbonylmethylide and three pyrrolo[2,1-b]isoquinoline compounds which were probably formed by addition of the primarily formed ylide, isoquinolinium trifluoromethyltrifluoroacetylmethylide, to 1.