OXIDATIONS OF 3,6-DIAMINO-1,2,4,5-TETRAZINE AND 3,6-BIS(S,S-DIMETHYLSULFILIMINO)-1,2,4,5-TETRAZINE

被引：43

作者：

COBURN, MD

HISKEY, MA

LEE, KY

OTT, DG

STINECIPHER, MM

机构：

[1] University of California, Los Alamos National Laboratory, Los Alamos, New Mexico

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1993年 / 30卷 / 06期

关键词：

D O I：

10.1002/jhet.5570300623

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1593 / 1595

页数：3

共 6 条

[1]

COBURN MD, 1986, SYNTHESIS-STUTTGART, P490

[2] AN IMPROVED SYNTHESIS OF 3,6-DIAMINO-1,2,4,5-TETRAZINE .2. FROM TRIAMINOGUANIDINE AND 2,4-PENTANEDIONE [J].