Abstract
A one-step synthesis of hard-to-reach adamantyl polyfluoroalkyl ethers in yields up to 95% comprises the reaction of strained 1,3-dehydroadamantane with polyfluorinated alcohols. In the competitive reactions of 1,3-dehydroadamantane with pentan-1-ol and its fluorinated analog, the latter compound is etherified predominantly (∼3:5).
References
J. Murata, S. Yamashita, M. Akiyama, S. Katayama, T. Hiaki, A. Sekiya, J. Chem. Eng. Data, 2002, 47, 911; DOI: https://doi.org/10.1021/je010322y.
A. Sekiya, S. Misaki, J. Fluorine Chem., 2000, 101, 215; DOI: https://doi.org/10.1016/S0022-1139(99)00162-1.
A. I. Rakhimov, O. V. Vostrikova, Izv. VolgGTU [Proceedings of the Volgograd State Technical University], 2010, 2, 44 (in Russian).
O. S. Andrienko, V. I. Sachkov, V. A. Yanovskiy, Prakticheskie metody vvedeniya ftora v organicheskie soedineniya [Practical Methods for Introducing Fluorine into Organic Compounds], Izd-vo Nauch.-Techn. Lit., Tomsk, 2010, 176 pp. (in Russian).
D. V. Danilov, V. S. D’yachenko, V. V. Burmistrov, G. M. Butov, I. A. Novakov, Russ. Chem. Bull., 2022, 71, 107; DOI: https://doi.org/10.1007/s11172-022-3383-8.
B. P. Gladkikh, D. V. Danilov, V. S. D’yachenko, V. V. Burmistrov, G. M. Butov, I. A. Novakov, Russ. Chem. Bull., 2022, 71, 1998; DOI: https://doi.org/10.1007/s11172-022-3620-1.
N. A. Elkina, E. V. Shchegolkov, Ya. V. Burgart, V. I. Saloutin, N. P. Boltneva, O. G. Serebryakova, S. V. Lushchekina, G. F. Makhaeva, Russ. Chem. Bull., 2021, 70, 567; DOI: https://doi.org/10.1007/s11172-021-3126-2.
N. A. Zefirov, A. V. Mamaeva, A. I. Krasnoperova, Yu. A. Evteeva, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, Russ. Chem. Bull., 2021, 70, 549; DOI: https://doi.org/10.1007/s11172-021-3123-5.
G. M. Butov, V. M. Mokhov, Russ. J. Org. Chem., 2014, 50, 447; DOI: https://doi.org/10.1134/S1070428014030270.
V. M. Mokhov, K. R. Saad, G. Yu. Parshin, G. M. Butov, Russ. J. Org. Chem., 2019, 55, 640; DOI: https://doi.org/10.1134/S1070428019050099.
G. M. Butov, V. M. Mokhov, Russ. J. Org. Chem., 2018, 54, 1760; DOI: https://doi.org/10.1134/S1070428018120035.
G. M. Butov, E. A. Zubovich, V. M. Mokhov, Russ. J. Org. Chem., 2020, 56, 1041; DOI: https://doi.org/10.1134/S1070428020060123.
S. V. Tarazanov, V. A. Shakun, T. N. Nesterova, V. S. Sarkisova, P. V. Naumkin, I. A. Nesterov, O. V. Repina, Petrol. Chem., 2018, 58, 895; DOI: https://doi.org/10.1134/S0965544118100171.
U.S. Pat. 5015758A, 1991; https://patents.google.com/patent/US5015758A/en.
G. Mlostoń, M. Celeda, K. Urbaniak, M. Jasiński, V. Bakhonsky, P. R. Schreiner, H. Heimgartner, Beilstein J. Org. Chem., 2019, 15, 497; DOI: https://doi.org/10.3762/bjoc.15.43.
A. I. Rakhimov, O. V. Vostrikova, Russ. J. Gen. Chem., 2011, 81, 374; DOI: https://doi.org/10.1134/S1070363211020150.
Jian-Bo Liu, **u-Hua Xu, Feng-Ling Qing, Org. Lett, 2015, 17, 5048; DOI: https://doi.org/10.1021/acs.orglett.5b02522.
Q. Yang, J. T. Njardarson, Tetrahedron Lett., 2013, 54, 7080; DOI: https://doi.org/10.1016/j.tetlet.2013.10.097.
J. Kalim, T. Duhail, E. Pietrasiak, E. Anselmi, E. Magnier, A. Togni, Chem. — Eur. J., 2020, 27, 1; DOI: https://doi.org/10.1002/chem.202005104.
G. M. Butov, V. M. Mokhov, Russ. J. Org. Chem., 2013, 49, 1403; DOI: https://doi.org/10.1134/S1070428013090303.
G. M. Butov, V. M. Mokhov, Russ. J. Org. Chem., 2018, 54, 1760; DOI: https://doi.org/10.1134/S1070428018120035.
R. E. Pincock, E. J. Torupka, J. Am. Chem. Soc., 1969, 91, 4593; DOI: https://doi.org/10.1021/ja01044a072.
DeLos F. DeTar, J. Am. Chem. Soc., 1982, 104, 7205; DOI: https://doi.org/10.1021/ja00389a051.
A. A. Rodriguez, C. T. Williams, J. R. Monnier, Catal. Lett., 2015, 145, 750; DOI: https://doi.org/10.1007/s10562-014-1464-5.
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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 664–668, March, 2023.
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Gladkikh, B.P., Mokhov, V.M., Butov, G.M. et al. Reactions of 1,3-dehydroadamantane with polyfluorinated alcohols. Russ Chem Bull 72, 664–668 (2023). https://doi.org/10.1007/s11172-023-3830-3
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DOI: https://doi.org/10.1007/s11172-023-3830-3