Unsaturated nitrogen compounds containing fluorine. Part II. The reactions of hexafluoroacetone azine with cis- or trans-but-2-ene and cyclohexene
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1059-1062
- https://doi.org/10.1039/p19720001059
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.Keywords
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