Abstract
Selective dimerization of styrene to 1,3-diphenylbutene-1 in the presence of [(acac)Pd(PAr3)2]BF4 + BF3OEt2 catalytic systems, where R = C6H5, o-CH3C6H4, p-CH3C6H4, or o-CH3OC6H4, has been studied. Under the optimal conditions (B/Pd = 8, T = 75°C, R = C6H5), the conversion of styrene to the products exceeds the conversion for the known analogs and reaches 1.5 tons of styrene/g-atom of palladium with amounts of dimers and trimers of 91 and 9%, respectively. The dimers consist of up to 100% 1,3-diphenylbutene-1 with a trans/cis isomer ratio of 95/5.
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S. M. Muthukumaru Pillai, M. Ravindranathan, and S. Sivaram, Chem. Rev. 86, 353 (1986).
J. Skupinska, Chem. Rev. 91, 613 (1991).
S. Hattori, H. Munakata, K. Tatsuoka, and T. Shimizu, FR Demande 2,193,803 (1977); Chem. Abstr. 82 (1975).
M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem. 21, 215 (1970).
K. Kawamoto, T. Imanaka, and S. Teranishi, Bull. Chem. Soc. Jpn. 44, 1239 (1971).
F. Dawans, Tetrahedron Lett. 22, 1943 (1971).
P. Grenouillet, D. Neibecker, and I. Tkatchenko, Organometallics 3, 1130 (1984).
K. Kaneda, T. Kiriyama, T. Hiraoka, and T. Imanaka, J. Mol. Catal. 48, 343 (1988).
J. R. Ascenso, M. A. A. F. Carrondo, A. R. Dias, et al., Polyhedron 8, 2449 (1989).
R. Faissner and G. Huttner, Eur. J. Inorg. Chem., No. 12, 2239 (2003).
J. Peng, J. Y. Li, H. Y. Qiu, et al., J. Mol. Catal. A: Chem. 255, 16 (2006).
A. Sen, T.-W. Lai, and R. R. Thomas, J. Organomet. Chem. 358, 567 (1988).
Z. Jiang and A. Sen, Organometallics 12, 1406 (1993).
W. P. Kretschmer, S. I. Troyanov, A. Meetsma, et al., Organometallics 17, 284 (1988).
T. Kondo, D. Tagaki, H. Tsujita, et al., Angew. Chem., Int. Ed. Engl. 46, 5958 (2007).
G. Myagmarsuren, V. S. Tkach, D. S. Suslov, and F. K. Shmidt, React. Kinet. Catal., Lett. 85, 197 (2005).
V. S. Tkach, D. S. Suslov, G. Myagmarsuren, and F. K. Shmidt, Zh. Prikl. Khim. 80, 1380 (2007).
M. L. Chernyshev, V.S. Tkach, T.V. Dmitrieva, et al., Kinet. Katal. 38, 575 (1997).
G. Myagmarsuren, Ki-Soo Lee, O-Yong Jeong, and Son-Ki Ihm, Polymer 45, 3227 (2004).
G. Myagmarsuren, Ki-Soo Lee, O-Yong Jeong, and Son-Ki Ihm, Polymer 46, 3685 (2005).
D. S. Suslov, Extended Abstract of Candidate’s Dissertation in Chemistry (Irkutsk, 2007).
G. Myagmarsuren, V. S. Tkach, F. K. Shmidt, et al., J. Mol. Catal. A: Chem. 235, 154 (2005).
V. S. Tkach, G. Myagmarsuren, M. Mesyef, and F. K. Shmidt, React. Kinet. Catal. Lett. 66, 281 (1999).
V. S. Tkach, D. S. Suslov, G. Myagmarsuren, et al., J. Organomet. Chem. 693, 2069 (2008).
A. A. Kashaev, V. S. Fundamenskii, A. V. Katkevich, et al., Dokl. Akad. Nauk 406, 765 (2006).
E. Schroder, G. Muller, and K.-F. Arndt, Polymer Characterization (Berlin, 1989), p. 212.
N. Ishihara, T. Seymiya, M. Kuramoto, and M. Uoi, Macromolecules 19, 2464 (1986).
C. Tolman, Chem. Rev. 77, 313 (1977).
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Original Russian Text © D.S. Suslov, V.S. Tkach, M.V. Bykov, M.V. Belova, 2011, published in Neftekhimiya, 2011, Vol. 51, No. 3, pp. 169–175.
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Suslov, D.S., Tkach, V.S., Bykov, M.V. et al. Selective dimerization of styrene to 1,3-diphenylbutene-1 in the presence of [(acac)Pd(PAr3)2]BF4/BF3OEt2 catalytic systems. Pet. Chem. 51, 157–163 (2011). https://doi.org/10.1134/S0965544111030157
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DOI: https://doi.org/10.1134/S0965544111030157