Abstract
The influence of the central metal atom and acid residue in a molecule of organometallic compound Ph3MX2 (M = Bi, Sb; X = Cl, Br, OAc, O2CEt) on the direction and yield of dephenylation products in a methyl acrylate— methanol system in the presence of Cu(OAc)2 and Na2PdCl2(OAc)2 was studied at 50 °C in acetonitrile. The main product of dephenylation of the antimony compounds is methyl cinnamate (yield 0.31–1.59 moles per mole of the starting Ph3SbX2), while anisole (0.55–0.97 mol) and halobenzene (0.67–1.04 mol) are those for compounds Ph3Bi(O2CR)2 and Ph3BiHal2, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J.-P. Finet, Ligand Coupling Reactions with Heteroatomic Compounds, Pergamon Press, Oxford, 1998, 291 pp.
I. B. Rabinovich, V. P. Nistratov, V. I. Tel’noi, and M. S. Sheiman, Termodinamika metalloorganicheskikh soedinenii [Thermodynamics of Organometallic Compounds], Izd-vo Nizhnii Novgorod Gos. Univ., Nizhnii Novgorod, 1996, 297 pp. (in Russian).
H. Suzuki and Y. Matano, Organobismuth Chemistry, Elsevier, New York, 2001, 619 pp.
A. V. Gushchin, D. V. Moiseev, and V. A. Dodonov, Izv. Akad. Nauk, Ser. Khim., 2001, 1230 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1291].
A. V. Gushchin, D. V. Moiseev, and V. A. Dodonov, Zh. Obshch. Khim., 2002, 72, 1669 [Russ. J. Gen. Chem., 2002, 72, 1571 (Engl. Transl.)].
D. V. Moiseev, A. V. Gushchin, A. S. Shavirin, Yu. A. Kursky, and V. A. Dodonov, J. Organomet. Chem., 2003, 667, 176.
D. V. Moiseev, V. A. Morugova, A. V. Gushchin, and V. A. Dodonov, J. Organomet. Chem., 2004, 689, 731.
V. A. Dodonov, A. V. Gushchin, and T. G. Brilkina, Zh. Obshch. Khim., 1984, 54, 2157 [J. Gen. Chem. USSR, 1984, 54 (Engl. Transl.)].
V. A. Dodonov, A. V. Gushchin, and T. G. Brilkina, Zh. Obshch. Khim., 1985, 55, 2514 [J. Gen. Chem. USSR, 1985, 55 (Engl. Transl.)].
V. A. Dodonov, T. I. Starostina, Yu. L. Kuznetsova, and A. V. Gushchin, Izv. Akad. Nauk, Ser. Khim., 1995, 156 [Russ. Chem. Bull., 1995, 44, 151 (Engl. Transl.)].
K. Matoba, S. Motofusa, C. S. Cho, K. Ohe, and S. Uemura, J. Organomet. Chem., 1999, 574, 3.
A. V. Gushchin, Doct. Sci. (Chem.) Thesis, Nizhnii Novgorod Gos. Univ., Nizhnii Novgorod, 1998, 283 pp. (in Russian).
D. V. Moiseev, Yu. B. Malysheva, A. S. Shavyrin, Yu. A. Kurskii, and A. V. Gushchin, J. Organomet. Chem., 2005, 690, 3652.
D. H. R. Barton, N. Ozbalik, and M. Ramesh, Tetrahedron, 1988, 44, 5661.
T. Ohe, T. Tanaka, M. Kuroda, C. S. Cho, K. Ohe, and S. Uemura, Bull. Chem. Soc. Jpn, 1999, 72, 1851.
K. A. Kocheshkov, A. P. Skoldinov, and N. N. Zemlyanskii, Metody elementoorganicheskoi khimii. Sur’ma, vismut [Methods of Organoelement Chemistry. Antimony, Bismuth], Nauka, Moscow, 1976, 483 pp. (in Russian).
V. A. Dodonov, A. V. Gushchin, and O. P. Bolotova, Zh. Obshch. Khim., 1990, 60, 2083 [J. Gen. Chem. USSR, 1990, 60 (Engl. Transl.)].
V. A. Dodonov and A. V. Gushchin, Izv. Akad. Nauk, Ser. Khim., 1993, 2043 [Russ. Chem. Bull., 1993, 42, 1955 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 655–658, April, 2006.
Rights and permissions
About this article
Cite this article
Gushchin, A.V., Korotkova, M.V., Malysheva, Y.B. et al. Dephenylation of triphenylbismuth(v) and antimony(v) derivatives in a methyl acrylate—methanol system in the presence of copper and palladium salts. Russ Chem Bull 55, 679–682 (2006). https://doi.org/10.1007/s11172-006-0312-1
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0312-1