Issue 19, 1975

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

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1975, 1902-1907

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

S. E. Armstrong, T. P. Forshaw and A. E. Tipping, J. Chem. Soc., Perkin Trans. 1, 1975, 1902 DOI: 10.1039/P19750001902

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements