Abstract
The main direction of hydrogenative ring-opening of propylcyclobutane on Pt/SiO2 catalyst in the temperature interval of 373–673 K is the formation of n-heptane through cleavage of the sterically hindered C1−C2 bond. The unusual selectivity can be attributed to adsorption of both the ring and the propyl group on the catalyst. With increasing temperature, the selectivity of ring-opening approaches the statistically expected ratio.
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R. Willstatter, J. Bruce: Ber.,40, 3979 (1907).
N. A. Rozanov: Zhur. Russk. Fiz. Khim. Obshch.,61, 2296 (1929).
S. E. Raik: Zhur. Obshch. Khim.,11, 324 (1941).
B. A. Kazanskii, M. Yu. Lukina: Dokl. Akad. Nauk SSSR.,74, 263 (1950).
M. Yu. Lukina, V. A. Ovodova, B. A. Kazanskii: Dokl. Akad. Nauk SSSR.,97, 683 (1954).
B. A. Kazanskii, M. Yu. Lukina, L. A. Nakhapetyan: Izv. Akad. Nauk SSSR. ser. khim., 1274 (1956).
M. Yu. Lukina, S. V. Zotova, B. A. Kazanskii: Dokl. Akad. Nauk SSSR.,116, 793 (1957).
B. S. Gudkov, A. A. Balandin: Dokl. Akad. Nauk SSSR.,162, 843 (1965).
M. Yu. Lukina, T. V. Olfereva, O. V. Bragin, A. L. Liberman, B. A. Kazanskii: Dokl. Akad. Nauk SSSR.,193, 106 (1970).
B. A. Kazanskii, O. V. Bragin, E. G. Khelkovskaya-Sergeeva, A. L. Liberman: Dokl. Akad. Nauk SSSR.,214, 103 (1974).
O. V. Bragin, E. G. Khelkovskaya-Sergeeva, S. V. Zotova, E. I. Vostokova, A. L. Liberman: Izv. Akad. Nauk SSSR. ser. khim. 363 (1974).
O. V. Bragin, E. G. Khelkovskaya-Sergeeva, A. V. Preobrazhenskii, A. L. Liberman: Izv. Akad. Nauk SSSR, ser. khim., 2023 (1975).
O. V. Bragin, E. G. Khelkovskaya-Sergeeva, A. L. Liberman: Izv. Akad. Nauk SSSR, ser. khim., 1037 (1979).
G. Maire, G. Ploudy, J. C. Prudhomme, F. G. Gault: J. Catal.,4, 556 (1965).
L. Hilaire, G. Maire, F. G. Gault: Bull. Soc. chim. France, 886 (1967).
G. Maire, F. G. Gault: Bull. Soc. chim. France, 894 (1967).
Z. Paál, M. Dobrovolszky: React. Kinet. Catal. Lett.,1, 435 (1974).
Z. Paál, M. Dobrovolszky, P. Tétényi: React. Kinet. Catal. Lett.,2, 97 (1975).
Z. Paál, P. Tétényi: Kémiai Közl.,43, 165 (1975).
H. C. Rowlinson, R. L. Burwell, Jr., R. H. Tuxworth: J. Phys. Chem.,59, 225 (1955).
H. Pines, J. Shabtai: J. Am. Chem. Soc.,83, 2781 (1961).
J. J. Rooney: J. Catal.,2, 53 (1963).
E. Sh. Finkel'shtein, A. I. Mikaya, V. M. Vdorin, N. S. Nametkin: Neftekhim.,16, 539 (1976).
D. A. Forsyth, S. Mahmoud, B. C. Giessen: Org. Magn. Reson.,19, 89 (1982).
J. K. A. Clarke, B. F. Hegarty, J. J. Rooney: J. Chem. Soc. Faraday Trans. I,84, 2511 (1988).
C. Zimmermann, K. Hayek: Proc. 10th International Congress on Catalysis, Budapest, 1992. P 234, p. 319.
J. Newham: Chem. Rev.,63, 123 (1963).
M. Yu. Lukina: Usp. Khim.,32, 1425 (1963).
O. V. Bragin, A. L. Liberman: Prevrashcheniya Uglevodorodov na Metallsoderzhashchikh Katalizatorakh, Khimiya, Moscow, 1981.
Z. Paál, P. Tétényi: in “Specialist Reports on Catalysis”, Vol. 5 (Eds G. C. Bond, G. Webb). The Royal Society of Chemistry, London, 1982.
M. Bartók, Á. G. Zsigmond: in “Stereochemistry of Heterogeneous Metal Catalysis”, Wiley, Chichester, 1985, p. 17.
M. Bartók, B. Kozma: Acta Chim. Hung.,55, 61 (1968).
M. Bartók, B. Kovács: Acta Chim. Hung.,56, 369 (1968).
M. Bartók, J. Apjok: Acta Phys. Chem., Szeged,21, 49 (1975).
I. Pálinkó, F. Notheisz, J. T. Kiss, M. Bartók: J. Mol. Catal.,77, 313 (1992).
M. Bartók, F. Notheisz, Á. G. Zsigmond: J. Catal.,63, 364 (1980).
F. Notheisz, M. Bartók: J. Catal.,71, 331 (1981).
G. V. Smith, M. Bartók, D. Ostgard, F. Notheisz: J. Catal.,101, 212 (1986).
M. Bartók, F. Notheisz, J. T. Kiss: J. Catal.68, 249 (1981).
R. Kramer: Kémiai Közl.,72, 34 (1991).
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Bartók, M., Török, B., Molnár, A. et al. Substituent effect in hydrogenative ring-opening of cyclobutanes on Pt/SiO2 . React Kinet Catal Lett 49, 111–118 (1993). https://doi.org/10.1007/BF02084036
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DOI: https://doi.org/10.1007/BF02084036