Ab Initio CALCULATIONS OF EFFECT OF (THIO)XANTHENYL
707
Scheme 4.
H
CH3COOH
Ph
+
Ph
CH2
NH
CH2
NH
HO
VI
VII
VIII
+
Ph
CH
N
−
IX
2. Yunnikova, L.P., Zh. Org. Khim., 1995, vol. 31, no. 1,
260, 270°C. Dibenzosuberenol is a commercial
product.
p. 76.
3. Yunnikova, L.P., Khim. Geterotsikl. Soed., 1995, no. 7,
N-Phenylmethyl-4-(5-dibenzo[a,d]cycloheptatri-
enyl)aniline (VIII). a. A mixture of 0.24 g (1.3 mmol)
of N-benzylaniline VI, 0.21 g (1 mmol) of dibenzo-
suberenol VII, and 4 ml of acetic acid was kept at
room temperature for 3 h. The reaction mixture was
diluted with water. The crystals were separated,
washed several times with water, and dried. Yield 0.22 g
p. 1003.
4. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E.,
Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr.,
Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M.,
Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B.,
Cossi, M., Scalmani, G., Rega, N., Petersson, G.A.,
Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R.,
Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y.,
Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E.,
Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C.,
Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O.,
Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W.,
Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P.,
Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S.,
Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K.,
Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V.,
Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J.,
Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P.,
Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-
Laham, M.A., Peng, C.Y., Nanayakkara, A., Сhalla-
combe, M., Gill, P.M.W., Johnson, B., Chen, W.,
Wong, M.W., Gonzalez, C., and Pople, J.A.,
GAUSSIAN 03, Rev. D.1, Gaussian, Inc., Wallingford,
CT, 2005.
1
(61.3%), mp 128–129°C (hexane). H NMR (CDCl3),
δ, ppm: 3.85 s (1H, NH), 4.18 s (2Н, CH2), 5.27 s (1Н,
С5Н), 6.31–7.43 m (19Н, АrН + С10Н, С11Н). Mass
spectrum, m/z (Irel, %): 373 [М]+(100); 282(15); 191
(19); 91(43); 77(3).
b. A mixture of 0.09 g (0.5 mmol) of N-benzyl-
aniline VI, 0.21 g (1 mmol) of dibenzosuberenol VII,
and 4 ml of acetic acid was kept at room temperature
for 4 h. The reaction mixture was diluted with water.
The crystals were separated, washed with water, dried,
and extracted with diethyl ether. The precipitated
compound IX was separated. Yield 0.006 g (3.2%), mp
186–187°C (benzene). From ether extract amine VIII
was isolated in a yield of 59%.
REFERENCES
1. Yunnikova, L.P., Makhova, T.V., Yunnikov, A.L., and
Gorokhov, V.Yu., Zh. Org. Khim., 2009, vol. 45, no. 5,
p. 749.
5. Kozlov, N.S., Pak, V.D., and Yunnikova, L.P., Zh. Org.
Khim., 1973, vol. 9, no. 4, p. 847.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 4 2013