Unsaturated nitrogen compounds containing fluorine. Part I. The thermal and photochemical reactions of hexafluoroacetone azine with acetylene and with hydrocarbon terminal olefins
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 2404-2408
- https://doi.org/10.1039/j39710002404
Abstract
Hexafluoroacetone azine reacts with ethylene, with propene, and with but-1-ene at 160—180° to give high yields of the corresponding 1 : 2 adducts, 1,5-diazabicyclo[3,3,0]octanes. Acetylene reacts similarly to give the corresponding 1,5-diazabicyclo[3,3,0]octa-2,6-diene. The olefins also react under photochemical conditions to give the same products, but acetylene does not react. The azine does not react with electron-deficient olefins or acetylenes under comparable conditions. Pyrolysis of the ethylene or propene adducts affords 3,3,3-trifluoro-2-trifluoromethylpropene in high yield; the acetylene adduct gives mainly a mixture of hexafluoroethane and 3,3,3-trifluoropropyne, together with 1,1,1,6,6,6-hexafluoro-2,5-bistrifluoromethylhexa-2,4-diene.Keywords
This publication has 0 references indexed in Scilit: