Accession Number : ADA192953

Title :   Research in Energetic Compounds.

Descriptive Note : Final rept. 1 Jan 78-31 Dec 87,

Corporate Author : FLUOROCHEM INC AZUSA CA

Personal Author(s) : Archibald, T A ; Garver, L C ; Malik, A A ; Bonsu, F O ; Tzeng, D D

PDF Url : ADA192953

Report Date : 09 Feb 1988

Pagination or Media Count : 79

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.

Descriptors :   *CYCLOBUTANES, *ENERGETIC PROPERTIES, *NITRATION, *EXPLOSIVES, BUTANES, ISOCYANATES, NITRATES, NITROGEN OXIDES, OXIDATION, POLYMERS, SILVER COMPOUNDS, SODIUM NITRITE, TETROXIDES

Subject Categories : Organic Chemistry
      Ammunition and Explosives

Distribution Statement : APPROVED FOR PUBLIC RELEASE