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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

“…Benzo-1,2,3,4-tetrazine 1,3-dioxide (BTDO) and its derivatives were brominated with DBI in CF 3 CO 2 H/H 2 SO 4 (5:1) or H 2 SO 4 , and mono- and polybromo-BTDOs were synthesized . Roeger et al used DBI in the synthesis of tetrasubstituted naphthalenediimides.…”

Progress in 1,2,3,4-Tetrazine Chemistry

“…The reduction of BTDOs was also studied. 39 37 Bromination of the parent BTDO 3a and 6-Br-BTDO gave a nearly equal ratio of isomers (Table 10). 8-Br-BTDO was brominated mainly at the 5-position.…”

“…Treatment of BTDOs with a HNO 3 /H 2 SO 4 mixture at room temperature resulted in 5-nitro and 7-nitro isomers 60 and 61 (Table 11). 37 The 60/61 isomer ratio depends on the substituents in the 6-and 8-positions. In the case of nitration of the parent BTDO 3a, the 7-nitro isomer is predominant.…”

“…A synthetic pathway to benzotetrazine 1,3-dioxides (BTDOs) 3 involves treatment of azoxy anilines 79 with nitrating agents (e.g., N 2 O 5 or NO 2 BF 4 ) in organic solvent 25,26,37,38 (Scheme 16).…”

Spectral assignments for 1H,13C and 15N solution and solid‐state NMR spectra of s‐tetrazine and dihydro‐s‐tetrazine derivatives

“…4 14 N measurements were also performed on oxidized 1,2,3,4-tetrazine systems but except in one case 13 the assignments were restricted to N-oxide and nitro groups. 2,3,8,9 In this paper, we present the 1 H, 13 C and 15 N NMR spectral assignment of a series of 3,6-disubstituted 1,2,4,5-tetrazine/dihydrotetrazine derivatives recently synthesized in our laboratory. Several new organic molecules and two polymers bearing the tetrazine moiety in the main chain were investigated using both solution and solid-state NMR methods.…”