BASICITY OF ISOMERIC DITETRAZOLYLBENZENES
595
%: C 44.42; H 2.84; N 52.65. C8H6N8. Calculated, %:
REFERENCES
C 44.86; H 2.8; N 52.34.
1. Butler, R.N. and Bhradaigh, E.P.N., J. Chem. Res.,
Synop., 1994, p. 149.
1,4-Bis(tetrazol-5-yl)benzene (III). mp 300°C.
1H NMR spectrum, δ, ppm: 8.22 m (4Harom). 13C NMR
spectrum, δC, ppm: 126.7, 127.9 (Carom); 155.4 (C5).
Found, %: C 45.14; H 3.27; N 52.86. C8H6N8. Cal-
culated, %: C 44.86; H 2.8; N 52.34.
2. Zubarev, V.Y., Trifonov, R.E., Filichev, V.V., Ostrov-
skii, V.A., Abell, A.D., and Edmonds, M.K., J. Chem.
Soc., Perkin Trans. 2, 2001, p. 417.
3. Fleming, A., Kelleher, F., Mahon, M.F., McGinley, J.,
1,2-Bis(2-tert-butyltetrazol-5-yl)benzene (IV).
1,2-Bis(tetrazol-5-yl)benzene (II), 1.3 g (0.006 mol),
was dissolved in 25 ml of 95% H2SO4, 0.020 mol of
t-BuOH was slowly added at 25°C, and the mixture
was vigorously stirred for 3 h at 25°C, diluted with
water, neutralized with a solution of NaOH, and ex-
tracted with CH2Cl2 (80 ml). The extract was dried
over anhydrous MgSO4 and evaporated, and the residue
was recrystallized from aqueous ethanol. Yield 1.53 g
and Prajapati, V., Tetrahedron, 2005, vol. 61, p. 7002.
4. Sauer, J., Huisgen, R., and Sturm, H., Tetrahedron,
1960, vol. 11, p. 241.
5. Abshire, G.J. and Marvel, C.S., Makromol. Chem.,
1961, vol. 44, p. 388.
6. Huisgen, R., Axen, C., and Seidl, H., Chem. Ber., 1965,
vol. 98, p. 2966.
7. Jursic, B. and Zdravkovski, Z., Synth. Commun., 1994,
vol. 24, p. 1575.
1
(78%), colorless crystals, mp 88.5–90.5°C. H NMR
8. Dyer, E. and Christie, P.A., J. Polym. Sci., Part A:
Polym. Chem., 1968, vol. 6, p. 729.
spectrum, δ, ppm: 1.62 s (18H, t-Bu), 7.71–7.90 m
(4H, Harom). 13C NMR spectrum, δC, ppm: 127.4,
130.2, 130.3 (Carom); 163.0 (C5); 28.7 [C(CH3)3]; 63.6
[C(CH3)3]. Found, %: C 59.39; H 7.16; N 34.80.
C16H22N8. Calculated, %: C 58.90; H 6.75; N 34.35.
9. Kaczmarek, J., Smagowski, H., and Grzonka, Z.,
J. Chem. Soc., Perkin Trans. 2, 1979, no. 12, p. 1670.
10. Koldobskii, G.I. and Ostrovskii, V.A., Usp. Khim.,
1994, vol. 63, p. 867.
1,3-Bis(2-tert-butyltetrazol-5-yl)benzene (V) was
11. Trifonov, R.E., Alkorta, I., Ostrovskii, V.A., and El-
guero, J., J. Mol. Struct. (Theochem), 2004, vol. 668,
p. 123.
synthesized in a similar way. Yield 1.37 g (70%),
1
colorless crystals, mp 114–115.5°C. H NMR spec-
trum, δ, ppm: 1.75 s (18H, t-Bu), 7.67–8.70 m (4H,
12. Ostrovskii, V.A. and Koren, A.O., Heterocycles, 2000,
H
arom). 13C NMR spectrum, δC, ppm: 123.7, 127.7,
vol. 53, p. 1421.
127.9, 129.7 (Carom); 162.8 (C5); 28.6 [C(CH3)3]; 63.8
[C(CH3)3]. Found, %: C 58.96; H 6.92; N 34.48.
C16H22N8. Calculated, %: C 58.90; H 6.75; N 34.35.
13. Bershtein, I.Ya. and Kaminskii, Yu.L., Spektrofotometri-
cheskii analiz v organicheskoi khimii (Spectrophoto-
metric Analysis in Organic Chemistry), Leningrad:
Khimiya, 1975, p. 167.
1,4-Bis(2-tert-butyltetrazol-5-yl)benzene (VI) was
synthesized in a similar way. Yield 1.25 g (64%),
14. Ostrovskii, V.A. and Koldobskii, G.I., Slabye organi-
cheskie osnovaniya (Weak Organic Bases), Leningrad:
Leningr. Gos. Univ., 1990, p. 52.
1
colorless crystals, mp 170–172.5°C. H NMR spec-
trum, δ, ppm: 1.76 s (18H, t-Bu), 8.23 m (4H, Harom).
13C NMR spectrum, δC, ppm: 127.1, 128.7 (Carom);
163.0 (C5); 28.8 [C(CH3)3], 64.1 [C(CH3)3]. Found, %:
C 59.10; H 6.55; N 34.68. C16H22N8. Calculated, %:
C 58.90; H 6.75; N 34.35.
15. Arnett, E.M., Joris, L., Mitchel, E., Murty, T.S.S.R.,
Gorrie, T.M., and Schleyer, P.v.R., J. Am. Chem. Soc.,
1970, vol. 92, p. 2365.
16. Berthelot, M., Laurence, C., Safar, M., and Besseau, F.,
J. Chem. Soc., Perkin Trans. 2, 1998, no. 2, p. 283.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 05-03-32366) using the equipment of the Regional
Research Center “Materials Science and Diagnostics in
Advanced Technologies.”
17. Cox, R.A. and Yates, K., Can. J. Chem., 1983, vol. 61,
p. 2225.
18. Tao, J., Ma, Z.-J., Huang, R.-B., and Zheng, L.S., Inorg.
Chem., 2004, vol. 43, p. 6133.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 4 2007