Novel synthesis of 3,4-dicyanofuroxan

Nitration of primary aminofurazans with aqueous nitric acid

“…Mass spectra were obtained on a Kratos MS 300 mass spectrometer (EI, 70 eV). Aminofurazans 2a, 19 2b, 20 2c, 6 2d, 21 2f, 22 and 4 23 were prepared according to the known procedures.…”

The first general synthesis of 3‐iodo‐4‐R‐furazans

“…The mixture was heated to reflux for 1 h, cooled, and the solvent was evaporated in a rotary evaporator. The residue was taken up in CH 2 Cl 2 (25 ml), washed with 5% aqueous K 2 CO 3 (3 × 5 ml), water (5 × 3 ml), dried with MgSO 4 (8). Amine 1d (1.05 g, 5 mmol) was added to nitrosylsulfuric acid prepared by dissolving NaNO 2 (0.35 g, 5 mmol) in H 2 SO 4 (4 ml) with efficient stirring in an ice bath.…”

“…• C. A sample was recrystallized from CCl 4 (3-Iodofurazan-4-yl)dichloroimine (6). To a solution of amine 1d (0.42 g, 2 mmol) in CCl 4 (10 ml) at room temperature, AlCl 3 (1.88 g, 0.014 mol) was added in a single portion with stirring under anhydrous conditions.…”

“…Thus, the first report of an iodofurazan was the synthesis of the parent 3-iodofurazan by reduction of 3,4-diiodofuroxan with SO 2 in ethanol described by Birckenbach and Sennewald in 1931 [2] As late as 1993, second and final compound, 3-iodo-4-methylfurazan 1a, was prepared by diazotization of 3-amino-4-methylfurazan 2a with NaNO 2 /H 2 SO 4 followed by treatment with aqueous solution of NaI; no iodo product could be obtained when other aminofurazans were exposed to the same reaction conditions [3]. A ring-cleavage reaction and triazene formation usually occurred when aminofurazans were diazotized under ordinary conditions [1,4]. Until now, no general methods for the direct transformation of the NH 2 -group at furazan ring to a halogen have been reported.…”

1H, 13C and 15N Nuclear Magnetic Resonance Analysis of 3,3’,4,4’-Diaminoazoxyfurazan Obtained by Oxidation of 3,4-Diaminofurazan with Peroxyformic Acid

“…diaminofurazan (mp. 180 °C [5]), 3-nitroso-4-aminofurazan (79 °C [8]), 3-nitro-4-aminofurazan (125 °C [2]). Francois et.…”