Accession Number : ADA337691

Title :   Improved Economical and Environmentally Benign Routes for the Large-Scale Synthesis of 1,3,3-Trinitroazetidine

Descriptive Note : Final rept. 15 Sep 96-31 Dec 97

Corporate Author : UNIVERSITY OF NORTH TEXAS DENTON DEPT OF CHEMISTRY

Personal Author(s) : Marchand, Alan P.

PDF Url : ADA337691

Report Date : 12 JAN 1998

Pagination or Media Count : 79

Abstract : Several routes for the synthesis of 1,3,3-trinitroazetidine (TNAZ) have been investigated. Of these the most promising new method involves studies of additions of various reagents, X-Y, across the highly strained C(3)-N sigma-bond in 3-ethyl-1-azabicyclo1.1.0butane. In the course of this study, it was found that reaction of this highly strained bicyclic amine with in situ generated HNO2 resulted in addition across the C(3)-N bond with concomitant N-nitrosation of the resulting intermediate azetidine, thereby affording N-nitroso-3-ethyl-3-nitro azacyclo butane (54%), which was oxidized subsequently to the corresponding dinitro azetidine, N-nitro-3-ethyl-3-nitro azacyclo butane (89%). These observations provide the basis of the method with which a novel synthesis of TNAZ has been developed. Our objectives include: (1) development of improved methods to permit scale-up of our previously published TNAZ synthesis, and (2) introduction of environmentally benign routes to prepare key synthetic intermediates.

Descriptors :   *SYNTHESIS(CHEMISTRY), *EXPLOSIVES, ENERGETIC PROPERTIES, X RAY SPECTROSCOPY, NITRO RADICALS, CYCLOBUTANES.

Subject Categories : Organic Chemistry
      Ammunition and Explosives

Distribution Statement : APPROVED FOR PUBLIC RELEASE