Research in Energetic Compounds.
Abstract
Alternate routes to 1,1,3,3-tetranitrocyclobutane were investigated. Attempts to nitrate or dephenylate 1,3-dinitro-2,4-diphenylcylobutane were unsuccessful. Ethyl 1,3-dinitrocyclobutane-1-carboxylate, obtained from ethyl bicyclo(1.1.0)butane-1-carboxylate and dinitrogen tetroxide, was treated with silver nitrate, sodium nitrite and base to give 1,1,3,3-tetra-nitrocyclobutane in 10 to 22% yield. 3,3-Dinitrocyclobutanecarboxylic acid, obtained via ethyl 3-oxocyclobutane-1-carboxylate oxime, was subjected to a Curtius reaction, conversion of the isocyanate to the amine, and oxidation to give, 1,1,3-trinitrocyclobutane. This compound decomposed under oxidative nitration conditions. Attempts to oxidize 3,3-dinitrocyclobutanol, obtained from the amine, were unsuccessful. 3,3-Dinitrocyclobutane-1,1-dicarboxylic acid was prepared from diethyl 3-oxocyclobutane-1,1-dicarboxylate. Keywords: Butanes, Cyclobutanes, Polymers.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 09, 1988
- Accession Number
- ADA192953
Entities
People
- A. A. Malik
- D. D. Tzeng
- F. O. Bonsu
- L. C. Garver
- T. A. Archibald