Abstract
The oxidation of dicyclopentadiene catalyzed by palladium(II) acetate and benzoquinone in the presence of perchloric acid was studied. Tricyclodecenone in high selectivity (85–98%) at a conversion of dicyclopentadiene up to 76% was obtained. The kinetic model assumed the significant inhibition complexation between dicyclopentadiene and tricyclodecenone with the catalytic species.
Similar content being viewed by others
References
L.A. Kheifits and S.I. Virezub, Zh. Obshch. Khim. 33 (1963) 2751.
L.A. Kheifits and S.I. Virezub, Zh. Obshch. Khim. 34 (1964) 2081.
L.A. Kheifits and S.I. Virezub, Zh. Org. Khim. 1 (1965) 1384.
US Patent 3 271 259 (1966).
Brit. Patent 1 143 425 (1966).
US Patent 3 598 745 (1971).
B. Cornils and R. Payer, Chem. Z. 2 (1974) 70.
B. Cornils, R. Payer, H. Tummes and J. Weber, Inf. Chem. 152 (1976) 149.
Ger. Patent 3 208 203 (1983).
Ger. Patent 3 501 888 (1986).
J. Tsuji, Synthesis 5 (1984) 369.
E. Stern, Catal. Rev. 1 (1968) 73.
J.E. Lyons, Appl. Ind. Catal. 3 (1984) 131.
K. Takehira, Kagaku Kogyo 38 (1987) 769; CA 107:200809k.
A.S. Abu-Surrah and B. Rieger, J. Mol. Catal. 128 (1998) 239.
A. Heumann, S. Kaldy and A. Tenaglia, Tetrahedron 50 (1994) 539.
Jap. Patent 26 244 (1987); CA 107:236133z.
K. Takehira, I.H. Oh, T. Hayakawa, H. Orita and M. Shimitzu, J. Mol. Catal. 53 (1989) 105.
K. Takehira, T. Hayakawa and H. Orita, Chem. Lett. (1985) 1835.
K. Takehira, H. Orita, I.H. Oh, C.O. Leobardo, G.C. Martinez, M. Shimitzu, T. Hayakawa and T. Ishikawa, J. Mol. Catal. 42 (1987) 247.
K. Takehira, T. Hayakawa, H. Orita and M. Shimitzu, in: Proc. Int. Symp. Dioxygen and Homogeneous Catal. Oxidat., Tsukuba, Vol. 33 (1988) p. 307.
K. Takehira, T. Hayakawa, H. Orita and M. Shimitzu, J. Mol. Catal. 53 (1989) 15.
K. Takehira, I.H. Oh, V.C. Martinez, R.S. Chavira, T. Hayakawa, H. Orita, M. Shimitzu and T. Ishikawa, J. Mol. Catal. 42 (1987) 237.
Jap. Patent 81 139 (1985); CA 103:087547a.
D.G. Miller and D.D.M. Wayner, J. Org. Chem. 55 (1990) 2924.
US Patent 5 120 877 (1992).
J. Chatt, L.M. Vallarino and L.M. Venanzi, J. Chem. Soc. (1957) 3413.
J.K. Stille and R.A. Morgan, J. Am. Chem. Soc. 88 (1966) 5135.
W. Todd Wipke and G.L. Goeke, J. Am. Chem. Soc. 96 (1974) 4244.
E. Balbolov and M. Skumov, Annual of the Higher Institute of Chemical Technology, Burgas, Vol. 28 (1993) 1.
S. Hansson, A. Heumann, T. Rein and B. Åkermark, J. Org. Chem. 55 (1990) 975.
R. Schmid and V.N. Sapunov, Non-Formal Kinetics (Verlag Chemie, Weinheim, 1982).
D.I. Kamenski and S.D. Dimitrov, Comput. Chem. Eng. 17 (1993) 643.
D.W. Marquardt, J. Soc. Ind. Appl. Math. 11 (1963) 431.
Rights and permissions
About this article
Cite this article
Skumov, M., Balbolov, E. Oxidation of dicyclopentadiene catalyzed by palladium(II) acetate and p-benzoquinone in the presence of inorganic acid. Catalysis Letters 69, 103–107 (2000). https://doi.org/10.1023/A:1019053402854
Issue Date:
DOI: https://doi.org/10.1023/A:1019053402854