1312
BEREZINA, FOMINA
N,N′-Bis[3-amino-2-phenyl-1H-inden-1-ylidene]-
J = 8.27 Hz). UV spectrum, λmax, nm (log ε): in
acetone: 435; in DMF: 424; in chloroform: 276 (5.21),
430 (4.17). Found, %: C.94; H 4.40; Cl 15.24; N 7.07.
C54H32Cl4N4. Calculated, %: C 73.8; H 3.64; Cl 16.17;
N 6.38.
2,2′-dinitrobiphenyl-4,4′-diamine (IVc). Yield 0.08 g
(53.3%), brick red crystalline substance which did not
melt up to 350°C, Rf 0.4; the product is soluble in
organic solvents and moderately soluble in water. IR
spectrum, ν, cm–1: 3417 (NH2), 1616 (C=N), 1514
(C=C, NO2), 1352 (NO2), 1188 (C–N), 1082 (C–C).
UV spectrum, λmax, nm: in acetone: 385; in DMF: 395;
in acetone–chloroform (1:1): 385. Found, %: C 67.86;
H 3.13; N 14.14; O 8.56. C42H28N6O4. Calculated, %:
C 74.12; H 4.12; N 12.35; O 9.41.
12,22,63,72-Tetranitro-41H,93H-3,5,8,10-tetraaza-
4,9(1,3)-diindena-1,2,6,7(1,4)-tetrabenzenacyclode-
caphane-3(41),93(10)-diene (Vc). Yield 0.2 g (31.7%),
red crystalline substance which did not melt up to 350°C,
Rf 0.7; the product is soluble in organic solvents and
moderately soluble in water. IR spectrum, ν, cm–1:
3455, 3158 (NH); 1633 (C=N), 1544 (NO2), 1078
12,22,63,72-Tetrasulfo-41H,93H-3,5,8,10-tetraaza-
4,9(1,3)-diindena-1,2,6,7(1,4)-tetrabenzenacyclode-
caphane-3(41),93(10)-diene (Va). A mixture of 9.1 mmol
of compound I and 0.87 mmol of 4,4′-diamino-
biphenyl-2,2′-disulfonic acid (IIa) or 36 mmol of
compound IIIa in 10 mL of DMF was heated for 55 h
under reflux. The mixture was cooled, and the
precipitate was filtered off, dried in air, and purified by
clumn chromatography on aluminum oxide using
acetone–chloroform (1 : 1) as eluent. Yield 0.2 g
(41.67%), bright red crystalline substance which did
not melt up to 350°C, Rf 0.58. IR spectrum, ν, cm–1:
3454, 3309 (NH); 3051 (OH); 1631, 1608 (C=N);
1543 (C=C), 1430 (S=O), 1155 (C–N), 1080 (C–C),
1
(C–C). H NMR spectrum, δ, ppm: 7.68 d (2H, J =
6.9 Hz), 7.6 d (4H, J = 7.5 Hz), 7.35–7.49 m (9H),
7.33 d (2H, NH, J = 4.98 Hz), 7.18 t (2H, J = 7.4 Hz).
UV spectrum, λmax, nm (log ε): in acetone: 406; in
DMF: 407; in acetone–chloroform (1 : 1): 344, 438; in
chloroform: 275 (5.02), 440 (4.08). Found, %: C
67.56; H 4.41; N 11.55. C54H32N8O8. Calculated, %: C
70.4; H 3.48; N 12.17.
REFERENCES
1. Smirnov, R.P., Berezina, G.R., Kolesnikov, N.A., and
Berezin, B.D., Izv. Vyssh. Uchebn. Zaved., Ser. Khim.
Khim. Tekhnol., 1986, vol. 29, no. 7, p. 3.
1
755 (C–O), 614 (C–S). H NMR spectrum, δ, ppm:
2. Berezina, G.R., Vorob’ev, Yu.G., and Smirnov, R.P., Zh.
7.66 d (4H, J = 7.5 Hz), 7.59 d (4H, J = 7.7 Hz), 7.35–
7.5 m (7H), 7.34 d (2H, NH, J = 4.95 Hz), 7.18 t (2H,
J = 7.4 Hz). UV spectrum, λmax, nm (log ε): in water:
451; in DMF: 342, 444; in ethanol: 341, 450; in
acetone–chloroform (1 : 1): 340, 444; in chloroform:
274 (5.14), 435 (4.24); in H2SO4: 359. Found, %:
C 63.20; H 4.73; N 5.68; O 16.55; S 11.57.
C54H36N4O12S4. Calculated, %: C 61.12; H 3.42; N
5.28; O 18.09; S 12.09.
Obshch. Khim., 1995, vol. 65, no. 12, p. 2036.
3. Berezina, G.R., Vorob’ev, Yu.G., and Smirnov, R.P.,
Russ. J. Gen. Chem., 1998, vol. 68, no. 6, p. 968.
4. Berezina, G.R., Vorob’ev, Yu.G., and Smirnov, R.P.,
Russ. J. Org. Chem., 1999, vol. 35, no. 5, p. 786.
5. Berezina, G.R., Vorob’ev, Yu.G., and Smirnov, R.P.,
Russ. J. Gen. Chem., 1999, vol. 69, no. 11, p. 1832.
6. Berezina, G.R., Vorob’ev, Yu.G., Vorob’eva, S.M., and
Andreikina, I.A., Russ. J. Gen. Chem., 2004, vol. 74,
no. 8, p. 1254.
7. Tietze, L.-F. and Eicher, T., Reactions and Syntheses in
the Organic Chemistry Laboratory, Mill Valley,
California: University Science Books, 1989. Translated
under the title Preparativnaya organicheskaya khimiya,
Moscow: Mir, 1999, p. 294.
Compounds Vb and Vc were synthesized in a
similar way.
13,23,62,73-Tetrachloro-41H,93H-3,5,8,10-tetraaza-
4,9(1,3)-diindena-1,2,6,7(1,4)-tetrabenzenacyclode-
caphane-3(41),93(10)-diene (Vb). Yield 0.1 g (25%),
dark red crystalline substance which did not melt up to
350°C, Rf 0.8; the product is readily soluble in organic
solvents and moderately soluble in water. IR spectrum,
ν, cm–1: 3454, 3312 (NH); 1544 (C=C), 1632 (C=N),
8. Tsiklicheskie β-diketony (Cyclic β-Diketones), Vanag, G.,
Ed., Riga: Akad. Nauk Latv. SSR, 1961, p. 207.
9. Nakamoto, K., Infra-Red Spectra of Inorganic and
Coordination Compounds, New York: Wiley, 1963.
1
10. Gordon, A.J. and Ford, R.A., The Chemist’s Com-
panion, New York: Wiley, 1972.
1159 (C–N), 1077 (C–C), 756 (C–Cl). H NMR
spectrum, δ, ppm: 7.69 d (4H, J = 7.69 Hz), 7.61 d
(6H, J = 7.6 Hz), 7.28–7.5 (14H), 7.26 d (2H, NH,
J = 5.11 Hz), 7.18 t (2H, J = 7.3 Hz), 6.93 t (6H,
11. Bellamy, L.J., Advances in Infra-Red Group Fre-
quencies, London: Methuen, 1966.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 7 2014