Azido and Tetrazolo 1, 2, 4, 5‐Tetrazine N‐Oxides. Issue 13 (23rd February 2017)

• Record Type: Journal Article
• Authors: Chavez, David E.; Parrish, Damon A.; Mitchell, Lauren; Imler, Greg H.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 13(2017)
• Page Start: 3575
• Page End: 3578
• Publication Date: 2017-02-23
• Subjects: 1, 2, 4, 5-tetrazine -- azides -- energetic materials -- N-oxides -- tetrazole; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201612496
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: This study presents the synthesis and characterization of the oxidation products of 3, 6‐diazido‐1, 2, 4, 5‐tetrazine (1 ) and 6‐amino‐[1, 5‐ b ]tetrazolo‐1, 2, 4, 5‐tetrazine (2 ). 3, 6‐Diazido‐1, 2, 4, 5‐tetrazine‐1, 4‐dioxide was produced from oxidation with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to two different products, 6‐amino‐[1, 5‐b]tetrazolo‐1, 2, 4, 5‐tetrazine mono‐N‐oxide and di‐N‐oxide. These N‐oxide compounds display promising performance properties as energetic materials. Abstract : The oxidation products of 3, 6‐diazido‐1, 2, 4, 5‐tetrazine (1 ) and 6‐amino‐[1, 5‐ b ]tetrazolo‐1, 2, 4, 5‐tetrazine (2 ) have been characterized. 3, 6‐Diazido‐1, 2, 4, 5‐tetrazine‐1, 4‐dioxide (see picture) was produced by oxidation of 1 with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to its mono‐ and di‐N‐oxide. These products display promising performance as energetic materials.