Oxidation of heterocyclic nitrogen yields to nitroheterocycles. [Nitrofurazans] Page: 4 of 8
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However, the 14N-NMR spectrum contained a very sharp singlet with a width at
half-height of 19 Hz and a chemical shift almost identical to that of J>.
Thus, it appears that we may have formed dinltrofurazan (10) 1n solution, but
we have not been able to Isolate 1t in pure form as yet (F1g. 2).
In addition, we have prepared a series of poly(dimethylsulfllimlo) he-
terocycles as potential precursors to polynitroheterocycles (F1g. 3). Oxida-
tion of 3,6-bis(dimethylsulf1l1mino)-l,2,4,5-tetrazine (11) with mcpba gave a
good yield of 3-dimethylsulfil1m1no-6-n1troso-l,2,4,5-tetraz1ne (12). Hy-
drolysis of 12 gave 3-amino-6-n1troso-l,2,4,5-tetrazine (13), which rapidly
polymerized to 1£ (Fig. 4).
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2. Hartman, G. D.; Schwering, J. E. J. Heterocycl. Chem. 1983, 20, 947.
3. Corey, E. 0.; Samuelsson, B.; Luzzlo, F. A. J. Am. Chem. Soc. 1984, 106,
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4. Hartman, G. 0.; Schwering, J. E.; Hartman, R. D. Tetrahedron Lett. 1983,
24, 1011.
5. Bodeker, J.; Kockritz, P. J. Prakt. Chem. 1978, 320, 1043.
6. Coburn, M. D. 0. Labelled Cornpds. (in press).
7. Westphal, G.; Schmidt, R. J. Prakt. Chem. 1973, 315, 791.
8. Hendrickson, J. B.; Schwartzman, S. M. Tetrahedron Lett., 1975, 277.
9. Schwartz, N. N.; Blumbergs, J. H. J. Org. Chem. 1964, 29, 1976.
10. Coburn, M. D.; J. Heterocyclic Chem. 1968, 5, 83.
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Coburn, Michael D. Oxidation of heterocyclic nitrogen yields to nitroheterocycles. [Nitrofurazans], article, January 1, 1985; New Mexico. (https://digital.library.unt.edu/ark:/67531/metadc1091172/m1/4/?rotate=90: accessed July 16, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.