Abstract
The [4+2] cycloaddition reactions of 1-alkyl-2,3,4,5-tetraphenylphosphole derivatives with N-phenylmaleimide were studied for the first time. The reactions of 1-alkyl-2,3,4,5-tetra-phenylphosphole oxides and sulfides with N-phenylmaleimide leads to tricyclic 10-phospha-norbornenes with high stereoselectivity, giving only one diastereomer in the racemic form. At the same time, 1-alkyl-2,3,4,5-tetraphenylphospholes and their W(CO)5L complexes do not undergo [4+2] cycloaddition reactions even upon prolonged heating.
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A. A. Zagidullin, I. A. Bezkishko, V. A. Miluykov, O. G. Sinyashin, Mendeleev. Commun., 2013, 23, 117.
F. Mathey, Acc. Chem. Res., 2004, 37, 954.
I. A. Bezkishko, A. A. Zagidullin, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Rev., 2014, (83), 555.
J. Grundy, F. Mathey, Angew. Chem., Int. Ed., 2005, 44, 1082.
H. Wang, C. Li, D. Geng, H. Chen, Z. Duan, F. Mathey, Chem. Eur. J., 2010, 16, 10659.
M. Zhi, Z. Gan, R. Ma, H. Cui, E.-Q. Li, Z. Duan, F. Mathey, Org. Lett., 2019, 21, 3210.
Z. Gan, M. Zhi, R. Han, E.-Q. Li, Z. Duan, F. Mathey, Org. Lett., 2019, 21, 2782.
F. Mercier, F. Brebion, R. Dupont, F. Mathey, Tetrahedron: Asymmetry, 2003, 14, 3137.
A. A. Zagidullin, E. S. Oshchepkova, I. V. Chuchelkin, S. A. Kondrashova, V. A. Miluykov, Sh. K. Latypov, K. N. Gavrilov, E. Hey-Hawkins, Dalton Trans., 2019, 48, 4677.
A. A. Zagidullin, V. A. Miluykov, O. G. Sinyashin, E. Hey-Hawkins, Catal Today., 2017, 279, 142.
A. Marinetti, F. Mathey, J. Fischer, A. Mitschler, J. Am. Chem. Soc., 1982, 104, 4484.
K. Lammertsma, A. Ehlers, M. McKee, J. Am. Chem. Soc., 2003, 125, 14750.
V. A. Miluykov, A. A. Zagidullin, O. G. Sinyashin, E. Hey-Hawkins, Russ. J. Coord. Chem., 2010, 36, 891.
J. Leitl, M. Marquardt, P. Coburger, D. J. Scott, V. Streitferdt, R. M. Gschwind, C. Muller, R. Wolf, Angew. Chem., Int. Ed., 2019, 58(43), 15407.
A. Loibl, I. Krom, E. Pidko, M. Weber, J. Wiecko, C. Muller, Chem. Commun., 2014, 50, 8842.
A. A. Zagidullin, Y. S. Ganushevich, A. G. Kafiyatullina, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Bull., 2015, 64, 1986.
C. Charrier, H. Bonnard, G. Lauzon, F. Mathey, J. Am. Chem. Soc., 1983, 105, 6871.
L. D. Quin, Curr. Org. Chem., 2006, 10, 43.
E. Mattmann, D. Simonutti, L. Ricard, F. Mercier, F. Mathey, J. Org. Chem., 2001, 66, 755.
E. Mattmann, F. Mercier, L. Ricard, F. Mathey, J. Org. Chem., 2002, 67, 5422.
A. Zagidullin, V. Miluykov, E. Oschepkova, A. Tufatullin, O. Kataeva, O. Sinyashin, Beilstein J. Org. Chem., 2015, 11, 169.
J. Svara, A. Marinetti, F. Mathey, Organometallics, 1986, 5, 1161.
S. Holand, F. Mathey, J. Org. Chem., 1981, 46, 4386.
T. Kovacs, L. S. Fulop, Z. Mucsi, K. Karaghiosoff, M. Czugler, G. Keglevich, Heteroat. Chem., 2015, 26, 335.
J. Kovacs, N. B. Szabo, Z. Nagy, K. Ludanyi, G. Keglevich, Heteroat. Chem., 2005, 16, 320.
A. Zagidullin, Y. Ganushevich, V. Miluykov, D. Krivolapov, O. Kataeva, O. Sinyashin, E. Hey-Hawkins, Org. Biomol. Chem., 2012, 10, 5298.
E. Oshchepkova, A. Zagidullin, T. Burganov, S. Katsyuba, V. Miluykov, O. Lodochnikova, Dalton Trans., 2018, 47, 11521.
A. V. Petrov, A. A. Zagidullin, T. I. Burganov, N. I. Shatalova, S. A. Katsyuba, V. A. Milyukov, Russ. Chem. Bull., 2019, 68, 445.
L. Nyul’aszi, Chem. Rev., 2001, 101, 1229.
A. Zagidullin, Y. Ganushevich, V. Miluykov, O. Sinyashin, E. Hey-Hawkins, Phosphorus, Sulfur, Silicon Relat. Elem., 2013, 188, 238.
A. Zagidullin, V. Miluykov, O. Sinyashin, P. Lonnecke, E. Hey-Hawkins, Heteroat. Chem., 2014, 25, 28.
L. Nyulaszi, O. Holloczki, C. Lescop, M. Hissler, R. Reau, Org. Biomol. Chem., 2006, 4, 996.
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This work was financially supported by the Russian Foundation for Basic Research and the Government of the Republic of Tatarstan in the framework of the scientific Project No. 18-43-160025.
The authors gratefully acknowledge the Assigned Spectral-Analytical Center for Study of Structure, Composition and Properties of Substances and Materials of FRC “Kazan Scientific Center of the Russian Academy of Sciences” for technical support of the research.
Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21—28, 2019, Moscow—Kazan, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0492—0495, March, 2020.
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Zagidullin, A.A., Grigoreva, E.S., Petrov, A.V. et al. [4+2] Cycloaddition reactions of 1-alkyl-2,3,4,5-tetraphenylphosphole derivatives. Russ Chem Bull 69, 492–495 (2020). https://doi.org/10.1007/s11172-020-2788-5
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DOI: https://doi.org/10.1007/s11172-020-2788-5