Synthesis of Novel 1-(4-Fluorophenyl diazoalkanes) and C,C-Disubstituted-N-(tetrafluoro-4-pyridyl)nitrones

Abstract

A valuable synthesis of novel dimer of C-(4-fluorophenyl)-C-methyl-N-(tetrafluoro-4-pyridyl)nitrone (9) and C,C-diphenyl-N-(tetrafluoro-4-pyridyl)nitrone (18) have been reported. The reaction of 2,3,5,6-tetrafluoro-4-nitrosopyridine (7) with a novel 1-(4- fluorophenyl diazoethane) (8a) in petroleum ether (40–60°C) affords the previous fluorinated nitrone (9) in good yield. In a similar fashion to that described, C,C-diphenyl-N-(tetrafluoro-4-pyridyl)nitrone (18) was synthesized in high yield (65%). The dipolar cycloaddition of this fluorinated nitrone to mono-substituted ethylene was unsuccessful.