SYNTHESIS AND PROPERTIES OF CADMIUM-CONTAINING QUINOLINIUM
was stirred for 15 min at 20 C, the solvent was re-
1075
REFERENCES
moved in vacuo at room temperature, and the residue
was washed in succession with ether and hexane and
dried in a vacuum desiccator over P2O5 to obtain
0.48 g of salt XIII. Compounds XIV XVIII were
synthesized in a similar way (Table 1).
1. Boev, V.I. and Dombrovskii, A.V., Khim. Geterotsikl.
Soedin., 1981, no. 7, pp. 881 886.
2. Boev, V.I. and Moskalenko, A.I., Zh. Obshch. Khim.,
1994, vol. 64, no. 7, pp. 1128 1133.
3. Boev, V.I. and Dombrovskii, A.V., Zh. Obshch. Khim.,
2-(Acetylmethyl)-1-phenylquinolinium perchlo-
rate (XXII). To a solution of 0.28 g of salt XVI in
3 ml of anhydrous CH2Cl2, 1 ml of acetic anhydride
and 0.1 g of anhydrous AlCl3 were added. The reaction
mixture was refluxed for 20 min with protection from
air moisture, treated with 5 ml of cold water, stirred
for 2 h, and filtered. The filtrate was treated with 2
ml of saturated aqueous sodium perchlorate. The light
rose precipitate that formed was filtered off, washed
in succession with water and ether, and dried at room
temperature to constant weight to obtain 0.16 g (93%)
of compound XXII, mp 161 163 C [11]. Salts XIX
XXI, XXIII and XXIV were synthesized in a similar
way.
1979, vol. 49, no. 11, pp. 2505 2508.
4. Yagupol’skii, L.M., Il’chenko, A.Ya, and Kondraten-
ko, N.V., Usp. Khim., 1974, vol. 43, no. 1, pp. 64 94.
5. Bellamy, L.J., The Infra-red Spectra of Complex
Molecules, London: Methuen, 1968. Translated under
the title Infrakrasnye spektry slozhnykh molekul,
Moscow: Inostrannaya Literatura, 1963, pp. 398 403,
251 252.
6. Balaban, A.T., Mateescu, I., and Ellian, M., Tetra-
hedron, 1962, vol. 18, no. 4, pp. 1083 1089.
7. Brown, D.W., Floyd, A.J., and Sainsbury, M., Orga-
nic Spectroscopy, Chichester: Wiley, 1988. Translated
under the title Spectroskopiya organicheskikh ve-
shchestv, Moscow: Mir, 1992, pp. 81 85.
4-(Trifluoroacetoxymercuriomethyl)-1-phenyl-
quinolinium perchlorate (XXV). A mixture of
0.5 mmol of salt XVII and 0.5 mmol of mercury(II)
trifluoroacetate in 2 ml of anhydrous ethanol was re-
fluxed for 30 min, 3 ml of saturated aqueous NaClO4
was added, and the resulting mixture was held over-
night in a refrigerator at 5 6 C. The precipitate that
formed was filtered off, washed with 5 ml of cold
water, and dried to constant weight to obtain 0.28
(95%) of compound XXV, mp 190 192 C [2].
8. Pauling, L. and Pauling, P., Chemistry, San Francisco:
Freeman, 1975. Translated under the title Khimiya,
Moscow: Mir, 1978, p. 156.
9. Yagupol’skii, L.M., Kondratenko, N.V., Klare, H.,
Bezdudnyi, A.V., and Yagupol’skii, Yu.L., Zh. Org.
Khim., 1999, vol. 35, no. 1, pp. 29 32.
10. Polyakova, A.A. and Khmel’nitskii, R.A., Mass-
spektrometriya v organicheskoi khimii (Mass Spec-
trometry in Organic Chemistry), Leningrad: Khimiya,
1972, pp. 243 249.
4-(Chlorostanniomethyl)-1-phenylquinolinium
chloride (XXVI). A mixture of 0.5 mmol of salt
XVII and 0.5 mmol of SnCl2 in 2 ml of anhydrous
ethanol was refluxed for 30 min. The ethanol was
removed at room temperature, and the residue was
washed with 5 ml of cold water and dried to constant
weight to obtain 0.071 g of salt XXVI. Compound
XXVII was synthesized in a similar way (Table 1).
11. Pilyugin, G.T. and Gutsulyak, B.M., Usp. Khim., 1963,
vol. 32, no. 4, pp. 389 432.
12. Dorofeenko, G.N., Sadekova, E.I., and Kuzne-
tsov, E.V., Preparativnaya khimiya piriliyevykh solei
(Preparative Chemistry of Pyrilium Salts), Rostov-on-
Don: Rost. Gos. Univ., 1972, p. 220.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 7 2001