Oxidations of 3,6‐diamino‐1,2,4,5‐tetrazine and 3,6‐bis( s,s ‐dimethylsulfilimino)‐1,2,4,5‐tetrazine | Zendy

Coburn M. D. | Zendy; Hiskey M. A. | Zendy; Lee K.Y. | Zendy; Ott D. G. | Zendy; Stinecipher M. M. | Zendy

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Oxidations of 3,6‐diamino‐1,2,4,5‐tetrazine and 3,6‐bis( s,s ‐dimethylsulfilimino)‐1,2,4,5‐tetrazine

Author(s) -

Coburn M. D.,

Hiskey M. A.,

Lee K.Y.,

Ott D. G.,

Stinecipher M. M.

Publication year - 1993

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570300623

Subject(s) - tetrazine , chemistry , dimethyldioxirane , medicinal chemistry , organic chemistry

Oxidation of 3,6‐diamino‐1,2,4,5‐tetrazine ( 1 ) with most peracids gave 3,6‐diamino‐1,2,4,5‐tetrazine 1,4‐dioxide ( 3 ) as the major product; however, treatment of 1 with peroxytrifluoroacetic acid (PTFA) gave 3,6‐diamino‐1,2,4,5‐tetrazine 1‐oxide ( 4 ) as the major product along with a small amount of 3‐amino‐6‐nitro‐1,2,4,5‐tetrazine 2,4‐dioxide ( 5 ). Oxidation of 3,6‐bis( S,S ‐dimethylsulfilimino)‐1,2,4,5‐tetrazine ( 6 ) with 3‐chloroperoxybenzoic acid (MCPBA) gave 3‐ S,S ‐(dimethylsulfilimino)‐6‐nitroso‐1,2,4,5‐tetrazine ( 7 ), which was oxidized further with dimethyldioxirane to 3‐( S,S ‐dimethylsulfoximino)‐6‐nitro‐1,2,4,5‐tetrazine ( 8 ). All attempts to obtain 3,6‐dinitro‐1,2,4,5‐tetrazine ( 2 ) by further oxidation of 7 or 8 failed.

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