Synthesis and Reaction of Tetranitroethylene

Article abstract of DOI:10.1021/jo00215a028

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.