Summary
-
1.
Like paraffins, benzene homologs can be cyclized in presence of platinized charcoal with formation of a five-membered ring. From propyl-, sec-butyl, and isobutyl-benzenes, indan and 1- and 2-metnylindans were obtained, respectively.
-
2.
The previously undescribed 3,5,6,7-tetrabromo-2-methylindan and 2,4,5,6,7-pentabromo-1-methylindene were prepared.
Similar content being viewed by others
Literature cited
B. A. Kazanskii, A. L. Liberman, T. F. Bulanova, V. T. Aleksanyan, and Kh. E. Sterin, Proc. Acad. Sci. USSR 95, 77 (1954); B. A. Kazanskii, A. L. Liberman, V. T. Aleksanyan and Kh. E. Sterin, Proc. Acad. Sci. USSR 95, 281 (1954); A. L. Liberman, T. V. Lapshina and B. A. Kazanskii, Proc. Acad. Sci. USSR 105, 727 (1955); A. L. Liberman, T. V. Vasina and B. A. Kazanskii, Proc. Acad. Sci. 117, 430 (1957).
M. Orchin, J. Amer. Chem. Soc. 68, 571 (1946).
W. E. Elwell, Chem. Abstrs. 45, 3422 (1951).
N. D. Zelinskii and I. N. Tits, Ber. 62, 2869 (1929); 59, 2591 (1926).
B. A. Kazanskii and T. F. Bulanova, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1948, 406; T. F. Bulanova, Thesis, Moscow, 1949.
A. L. Liberman, O. V. Bragin and B. A. Kazanskii, Proc. Acad. Sci. 111, 1039 (1956).
F. D. Rossini et al., Selected Values of Physical and Thermodynamic Properties of Hydrocarbons and Related Compounds, Pittsburgh, Ohio, U.S.
E. B. Evans, J. Inst. Petroleum Techn. 24, 537 (1938).
P. A. Plattner and J. Wyss, Helv. chim. acta 24, 483 (1941).
R. Paul and S. Tchelitcheff, Bull. Soc. chim. France, 1948, 108.
L. Ya. Bryusova and E. S. Shuvalov, Collection: Syntheses of Perfumes, Food Ind. Press, Moscow, 1939, p. 185. [in Russian].
A. Klages, Ber. 37, 1723 (1904).
B. A. Kazanskii, A. L. Liberman, A. F. Plate, M. I. Rozengart and O. D. Sterligov, Proc. Acad. Sci. USSR 71, 477 (1950).
P. Amagat, Bull. Soc. chim. France (4), 41, 940 (1927).
N. D. Zelinskii, K. Pakendorf and L. Leder-Pakendorf, Ber. 67, 300 (1934).
M. M. Jamison, M. S. Lesslie and E. E. Turner, J. Inst. Petrol. 35, 307 (1949).
R. Meyer, and W. Meyer, Ber. 51, 1581 (1918).
N. D. Zelinskii and M. B. Turova-Polyak, Selected Works of Academician N. D. Zelinskii, 2, Izd. AN SSSR, Moscow and Leningrad, 1941, pp. 150, 224. [in Russian].
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Liberman, A.L., Bragin, O.V. & Kazanskii, B.A. Catalytic cyclization of some alkylbenzenes into indan and its homologs. Russ Chem Bull 8, 846–854 (1959). https://doi.org/10.1007/BF00915913
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00915913