Improved Economical and Environmentally Benign Routes for the Large-Scale Synthesis of 1,3,3-Trinitroazetidine
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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 12, 1998
- Accession Number
- ADA337691
Entities
People
- Alan P. Marchand
Organizations
- University of North Texas