Unsaturated nitrogen compounds containing fluorine. Part VI. Reactions of hexafluoroacetone azine with 2-methylbut-2-ene, 2,3-dimethylbut-2-ene, 2,3-dimethylbut-1-ene, and cyclopentene
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 19,p. 1902-1907
- https://doi.org/10.1039/p19750001902
Abstract
The thermal reaction of hexafluoroacetone azine with 2-methylbut-2-ene gives nitrogen, 1,1,1,3,3,3-hexafluoropropane, a mixture (32%) of eight bis(trifluoromethyl)carbene–olefin adducts including the alkene (CF3)2C:CH·CHMeEt (7%) and the cyclopropane (CF3)2[graphic omitted]HMe (13%), and tar. In contrast the reaction with 2,3-dimethylbut-2-ene gives mainly the 1:1 adduct (CF3)2C:N·NH·C(CF3)2·CH2·CMe:CMe2, but nitrogen, 1,1,1,3,3,3-hexafluoropropane, and the carbene–olefin adducts (CF3)2C:CH·CHMe·CHMe2(2%), (CF3)2CH·[graphic omitted]H·CHMe2(7%), and (CF3)2CH·CH2·CMe:CMe2(15%) are also formed; the reaction with 2,3-dimethylbut-1-ene gives the same products, together with the cyclopropane (CF3)2[graphic omitted]Me·CHMe2, and the recovered olefin fraction from both reactions contained the but-2-ene and the but-1-ene in the ratio ca. 4:1. The reaction with cyclopentene gives the Δ3-pyrazoline [graphic omitted]·CH(CF3)2(63%), together with nitrogen, 1,1,1,3,3,3-hexafluoropropane, and the carbene–olefin adducts (CF3)2CH·[graphic omitted]H2 and (CF3)2C:[graphic omitted]H2.Keywords
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