Unsaturated nitrogen compounds containing fluorine. Part II. The reactions of hexafluoroacetone azine with cis- or trans-but-2-ene and cyclohexene

Abstract

Hexafluoroacetone azine reacts with but-2-ene or cyclohexene under thermal conditions to give products formally derived from the intermediacy of bis(trifluoromethyl)carbene. Thus cis- or trans-but-2-ene afford a mixture of cis- and trans-2,3-dimethyl-1,1-bis(trifluoromethyl)cyclopropane in the ratio ca. 1 : 4 and cyclohexene gives 7,7-bis(trifluoromethyl)norcarane and the allylic insertion compound, 3-(2,2,2-trifluoro-1-trifluoromethylethyl)-cyclohexene, in the ratio ca. 2 : 5. Pyrolysis of the trans-cyclopropane gives 1,1,1-trifluoro-2-methyl-2-trifluoro-methylpent-2-ene and 1,1-bis(trifluoromethyl)propa-1,2-diene among the products.