Abstract
The kinetics and chemoselectivity of cycloalumination of 1-octene and 4-octyne with Et3Al in the presence of a catalytic amount of Cp2ZrCl2 in hexane at various temperatures and ratios between reactants was studied. It was found that chemoselectivity for the formation of aluminacyclopentanes and aluminacyclopentenes was improved and the reaction time was significantly shortened when the cycloalumination reaction was carried out at an elevated temperature (40°C) and an equimolar ratio between an unsaturated compound (4-octyne or 1-octene) and Et3Al. Quantitative characteristics of the reactivity of a number of alkenes and alkynes, including functionally substituted ones, were obtained.
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REFERENCES
Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., Muslukhov, R.R., and Tolstikov, G.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, p. 207.
Ibragimov, A.G., Khim. Interesah Ustoich. Razvit., 2008, vol. 16, no. 6, p. 715.
D’yakonov, V.A., Dzhemilev Reaction in Organic and Organometallic Synthesis (New York: Nova Science, 2010).
D’yakonov, V.A., Ibragimov, A.G., Khalilov, L.M., Makarov, A.A., Timerkhanov, R.K., Tuktarova, R.A., Trapeznikova, O.A., and Galimova, L.F., Chem. Heterocycl. Compd., 2009, vol. 45, p. 317.
D’yakonov, V.A., Tuktarova, R.A., Islamov, I.I., Khalilov, L.M., and Dzhemilev, U.M., Steroids, 2016, vol. 108, p. 77.
D’yakonov, V.A., Makhamatkhanova, A.L., Agliullina, R.A., Dilmukhametova, L.K., Tyumkina, T.V., and Dzhemilev, U.M., Beilstein J. Org. Chem., 2016, vol. 12, p. 406.
D’yakonov, V.A., Makhamatkhanova, A.L., Dilmukhametova, L.K., Agliullina, R.A., Tyumkina, T.V., and Dzhemilev, U.M., Organometallics, 2014, vol. 34, p. 221.
Abakumov, G.A., Piskunov, A.V., Cherkasov, V.K., Fedushkin, I.L., Ananikov, V.P., Eremin, D.B., Gordeev, E.G., Beletskaya, I.P., Averin, A.D., Bochkarev, M.N., Trifonov, A.A., Dzhemilev, U.M., D’yakonov, V.A., Egorov, M.P., Vereshchagin, A.N., Syroeshkin, M.A., Jouikov, V.V., Muzafarov, A.M., Anisimov, A.A., Arzumanyan, A.V., et al., Russ. Chem. Rev., 2018, vol. 87, no. 5, p. 393.
D’yakonov, V.A., Trapeznikova, O.A., de Meijere, A., and Dzhemilev, U.M., Chem. Rev., 2014, vol. 114, p. 5775.
Ramazanov, I.R., Kadikova, R.N., and Dzhemilev, U.M., Russ. Chem. Bull., 2011, vol. 60, no. 1, p. 99.
Negishi, E.-i., Kondakov, D.Y., Choueiry, D., Kasai, K., and Takahashi, T., J. Am. Chem. Soc., 1996, vol. 118, p. 9577.
Tyumkina, T.V., Islamov, D.N., Parfenova, L.V., Karchevsky, S.G., Khalilov, L.M., and Dzhemilev, U.M., Organometallics., 2018, vol. 37, p. 2406.
Balaev, A.V., Parfenova, L.V., Gubaidullin, I.M., Rusakov, S.V., Spivak, S.I., Khalilov, L.M., and Dzhemilev, U.M., Dokl. Phys. Chem., 2001, vol. 381, nos. 1–3, p. 279.
Dzhemilev, U.M., Ibragimov, A.G., and Zolotarev, A.P., Mendeleev Commun., 1992, vol. 2, p. 135.
Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., Muslukhov, R.R., and Tolstikov, G.A., Izv. Akad. Nauk, Ser. Khim., 1990, no. 12, p. 2831.
Parfenova, L.V., Gabdrakhmanov, V.Z., Khalilov, L.M., and Dzhemilev, U.M., J. Organomet. Chem., 2009, vol. 694, p. 3725.
Funding
This work was supported by the Russian Foundation for Basic Research (grant no. 18-03-00817) and the Institute of Petrochemistry and Catalysis, Russian Academy of Sciences (state contract nos. AAAA-A19-119022290007-9 and AAAA-A19-119022290008-6, 2019–2021).
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Translated by V. Makhlyarchuk
Abbreviations: δ, chemical shifts.
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Ramazanov, I.R., Kadikova, R.N. Kinetics of Zr-Catalyzed Cycloalumination of Alkenes and Alkynes in the Dzhemilev Reaction. Kinet Catal 61, 106–111 (2020). https://doi.org/10.1134/S0023158420010085
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DOI: https://doi.org/10.1134/S0023158420010085