73804-83-8Relevant academic research and scientific papers
Synthesis and Reaction of Tetranitroethylene
Baum, Kurt,Tzeng, Dongjaw
, p. 2736 - 2739 (1985)
Tetranitroethylene was isolated in 50 percent yield by flash vacuum pyrolysis of heksanitroethane.Critical for the isolation is a trap temperature such that dinitrogen tetraoxide is not condensed.Tetranitroethylene reacted quantitatively with anthracene to give 11,11,12,12,-tetranitro-9,10-dihydro-9,10-ethanoanthracene, and competition experiments with anthracene showed that tetranitroethylene is at least an order of magnitude more reactive than tetracyanoethylene.Tetranitroethylene reacted with cyclopentadiene to give 5,5,6,6-tetranitronorbornene and with ethanolto give ethyl dinitroacetate.Acetylenes and olefins reacted with tetranitroethylene to give 3-nitroisoxazoles and 3-nitro-2-isoxazolines, respectively.
Tetranitroethylene. In Situ Formation and Diels-Alder Reactions
Griffin, T. Scott,Baum, Kurt
, p. 2880 - 2883 (2007/10/02)
The reaction of hexanitroethane with dienes gave the Diels-Alder adducts of tetranitroethylene.Thus, the reaction in refluxing benzene of hexanitroethane with anthracene gave 11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene.Similarly, 9-methylanthracene and 9,10-dimethylanthracene gave 9-methyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene and 9,10-dimethyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene, respectively.Cyclopentadiene reacted with hexanitroethane in methylene chloride at -10 deg C to give 5,5,6,6-tetranitro-2-norbornene.Reaction of the anthracene adduct of tetranitroethylene with sodium iodide gave the sodium salt of 12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, which was protonated with acetic acid to give the corresponding nitro ketone.Treatment of the sodium salt with clorine and bromine gave 12-chloro-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one and 12-bromo-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, respectively.
