Unsaturated nitrogen compounds containing fluorine. Part III. Reactions of hexafluoroacetone azine with alkanes, cycloalkanes, and trimethylsilane

Abstract

Hexafluoroacetone azine reacts with cyclopentane at 140 °C to give nitrogen, 1,1,1,3,3,3-hexafluoropropane, (2,2,2-trifluoro-1-trifluoromethylethyl)cyclopentane, 2-(cyclopentylazo)-1,1,1,3,3,3-hexafluoropropane, 4,4a,5,6,7,7a-hexahydro-3,4,4-tris(trifluoromethyl)-1H-cyclopenta[c]pyridazine, and tar; at higher temperatures the azo-compound is not present. The corresponding reactions with cyclobutane, cycloheptane, 2-methylpropane, 2-methylbutane, 2-methylpentane, and trimethylsilane are also reported. The major products from the last reactions are hexafluoroacetone (2,2,2-trifluoro-1-trifluoromethylethyl)hydrazone and N-trimethylsilylhexafluoroisopropylideneamine in the ratio ca. 1 : 2.