ADAMANTYLAZOLES: XIV.
2373
Uspekhi khimii adamantana (Survey of Modern
Chemistry in Russia. Advances in the Chemistry of
Adamantane), Moscow: Khimiya, 2007, p. 89.
NMR spectrum, δ, ppm: 3.51 s (3H, Me), 2.22 s (3H,
Ad), 2.15 s (6H, Ad), 1.73 s (6H, Ad). Found, %: C
60.92; H 8.64; N 28.36. C12H19N5. Calculated, %: C
61.80; H 8.15; N 30.04.
3. Logvinov, A.V., Polyakova, I.N., and Golod, E.L., Russ.
J. Gen. Chem., 2009, vol. 79, no. 10, p. 2220.
1-(1-Adamantyl)-3-methyltetrazolium-5-aminide
(Xc). Yield 99%, mp 181–183°C (from hexane–
benzene, 1 : 2). 1H NMR spectrum, δ, ppm: 3.92 s (3H,
Me), 2.29 s (6H, Ad), 2.16 s (3H, Ad), 1.71 s (6H, Ad).
Found, %: C 61.47; H 7.79; N 30.15. C12H19N5.
Calculated, %: C 61.80; H 8.15; N 30.04.
4. Henry, R.A. and Finnegan, W.G., J. Am. Chem. Soc.,
1954, vol. 76, no. 3, p. 923.
5. Spear, R.J., Aust. J. Chem., 1984, vol. 37, no. 12,
p. 2453.
6. Voitekhovich, S.V., Gaponik, P.N., Lyakhov, A.S., and
Ivashkevich, L.S., Tetrahedron, 2008, vol. 64, no. 37,
p. 8721.
7. Henry, R.A., Finnegan, W.G., and Lieber, E., J. Am.
Chem. Soc., 1954, vol. 76, no. 11, p. 2894.
1,3-Bis(1-adamantyl)-5-aminotetrazolium chloride
1
(XIa). mp 221°C (decomp., from i-PrOH). H NMR
spectrum, δ, ppm: 8.29 s (2H, NH2), 2.28 s (9H, Ad),
2.23 s (9H, Ad), 1.85–1.68 m (12H, Ad). Found, %: C
64.68; H 8.35; N 17.85. C21H32ClN5. Calculated, %: C
64.70; H 8.21; N 17.97.
8. Moderhack, D. and Holtmann, B., J. Prakt. Chem.,
2000, vol. 342, no. 6, p. 591.
9. Bocian, W., Jazwinski, J., Kozminski, W., Stefaniak, L.,
and Webb, G.A., J. Chem. Soc., Perkin Trans. 2, 1994,
no. 6, p. 1327.
3-(1-Adamantyl)-5-amino-1-methyltetrazolium
chloride (XIb). mp 212°C (decomp., from i-PrOH).
1H NMR spectrum, δ, ppm: 8.69 s (2H, NH2), 4.06 s
(3H, Me), 2.27 s (3H, Ad), 2.23 s (6H, Ad), 1.75 s (6H,
Ad). Found, %: C 52.93; H 7.65; N 25.92. C12H20ClN5.
Calculated, %: C 53.43; H 7.42; N 25.97.
10. Karaghiosoff, K., Klapötke, T.M., Mayer, P., Piotrowski, H.,
Polborn, K., Willer, R.L., and Weigand, J.J., J. Org.
Chem., 2006, vol. 71, no. 4, p. 1295.
11. Araki, S., Yamamoto, K., Yagi, M., Inoue, T.,
Fukagawa, H., Hattori, H., Yamamura, H., Kawai, M.,
and Butsugan, Y., Eur. J. Org. Chem., 1998, vol. 1998,
no. 1, p. 121.
1-(1-Adamantyl)-5-amino-3-methyltetrazolium
chloride (XIc). mp 201°C (decomp., from i-PrOH). 1H
NMR spectrum, δ, ppm: 8.34 s (2H, NH2), 4.31 s (3H,
Me), 2.25 s (6H, Ad), 2.22 s (3H, Ad), 1.85–1.67 m
(6H, Ad). Found, %: C 52.68; H 7.28; N 25.54.
C12H20ClN5. Calculated, %: C 53.43; H 7.42; N 25.97.
12. Klapötke, T.M., Sabaté, C.M., and Stierstorfer, J.,
Z. Anorg. Allg. Chem., 2008, vol. 634, no. 11, p. 1867.
13. Klapötke, T.M., Karaghiosoff, K., Mayer, P., and
Welch, J.M., Propellants, Explos., Pyrotech., 2006,
vol. 31, no. 3, p. 188.
1-(1-Adamantyl)-4-phenyl-4,5-dihydro-1H-tetra-
zol-5-imine (XII). Yield 77%, mp 115–116°C (from
50% i-PrOH). 1H NMR spectrum, δ, ppm: 7.53–7.40 m
(5H, Ph), 5.19 s (1H, NH), 2.33 s (6H, Ad), 2.19 s (3H,
Ad), 1.75–1.72 m (6H, Ad). Found, %: C 69.47; H
7.55; N 23.43. C17H21N5. Calculated, %: C 69.15; H
7.12; N 23.73.
14. Karaghiosoff, K., Klapötke, T.M., Mayer, P., Sabaté, C.M.,
and Penger, A., Inorg. Chem., 2008, vol. 47, no. 3,
p. 1007.
15. Klapötke, T.M. and Sabaté, C.M., Chem. Mater., 2008,
vol. 20, no. 5, p. 1750.
16. Klapötke, T.M. and Sabaté, C.M., Eur. J. Inorg. Chem.,
2008, no. 34, p. 5350.
17. APEX2 (Version 2008.6-1), SAINT (Version 7.60A),
SADABS-2008/1, Madison, Wisconsin, USA: Bruker
AXS.
1-(1-Adamantyl)-5-amino-4-phenyltetrazolium
chloride (XIII). mp 205°C (decomp., from i-PrOH).
1H NMR spectrum, δ, ppm: 9.14 s (2H, NH2), 7.69 s
(5H, Ph), 2.37 s (6H, Ad), 2.26 s (3H, Ad), 1.92–1.69
m (6H, Ad). Found, %: C 61.97; H 6.09; N 21.08.
C17H22ClN5. Calculated, %: C 61.54; H 6.64; N 21.12.
18. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008,
vol. 64, no. 2, p. 112.
19. Allen, F.H., Acta Crystallogr., Sect. B, 2002, vol. 58,
no. 3, p. 380.
20. Voitekhovich, S.V., Vorob’ev, A.N., Gaponik, P.N., and
Ivashkevich, O.A., Khim. Geterotsikl. Soedin., 2005,
no. 8, p. 1174.
REFERENCES
1. Logvinov, A.V., Polyakova, I.N., and Golod, E.L., Russ.
J. Gen. Chem., 2009, vol. 79, no. 10, p. 2230.
21. Gaponik, P.N., Karavai, V.P., and Grigor’ev, Yu.V.,
Khim. Geterotsikl. Soedin., 2005, no. 8, p. 1174.
2. Golod, E.L., Panorama sovremennoi khimii Rossii.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 11 2010