Abstract
Ways of synthesizing dichloro-[2,2]-paracyclophane (dichloroPCP), a valuable monomer for the manufacturing of polymeric coating used in radioelectronics, are described. There are currently no plants for its production in Russia. Analysis of the considered methods of synthesis show the Hofmann elimination of quaternary ammonium salts is the best technique for the industrial production of dichloroPCP. A promising way of conducting the four-stage synthesis of this product in practice is to use such catalytic technologies as catalysis with alkalis and Lewis acids.
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REFERENCES
Brown, C.J. and Farthing, A.C., Nature, 1949, vol. 164, no. 4178, pp. 915–916.
Paradies, J., Synthesis, 2001, no. 23, pp. 3749–3766.
CN Patent 103613618, 2015.
David, O.R.P., Tetrahedron, 2012, vol. 68, no. 44, pp. 8977–8993.
Gibson, S.E. and Knight, J.D., Org. Biomol. Chem., 2003, vol. 1, pp. 1256–1269.
Takenaga, N., Adachi, S., Furusawa, A., Nakamura, K., Suzuki, N., Ohta, Y., Komizy, M., Mukai, C., and Kitagaki, S., Tetrahedron, 2016, vol. 72, no. 43, pp. 6892–6897.
Bisai, V. and Singh, V.K., Tetrahedron Lett., 2016, vol. 57, no. 43, pp. 4771–4784.
Modern Cyclophane Chemistry, Hopf, H. and Gleiter, R., Eds., Weinheim: Wiley-VCH, 2004.
De Meijere, A. and König, B., Synlett, 1997, no. 11, pp. 1221–1232.
US Patent 3342754, 1967.
Hopf, H., Angew. Chem., Int. Ed. Engl., 2008, vol. 47, pp. 9808–9812.
Vögtle, F. and Neumann, P., Synthesis, 1973, no. 2, pp. 85–103.
US Patent 3149175, 1964.
US Patent 3247274, 1966.
US Patent 3258504, 1966.
US Patent 34400295, 1969.
RF Patent 2043323, 1992.
Shevel’kova, L.V., Sokolovskaya, V.G., and Gusel’nikov, L.E., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1993, vol. 36, no. 7, pp. 80–87.
Kawakami, S., Iwaki, S., Nakada, M., and Yamaguchi, T., Bull. Chem. Soc. Jpn., 1991, vol. 64, no. 3, pp. 1000–1004.
US Patent 2013/0109827, 2013.
Kirk-Othmer Encyclopedia of Chemical Technology, New York: Wiley, 1999, vol. 26, 4th ed.
Kardash, I.E., Pebalk, A.V., and A.V. Pravednikov, Itogi Nauki Tekh., Ser.: Khim. Tekhnol. Vysokomol. Soedin., 1984, vol. 19, p. 84.
Otsubo, T., Mizogami, S., Sakata, Y., and Misumi, S., Tetrahedron Lett., 1973, vol. 14, no. 27, pp. 2457–2460.
Pan, D., Wang, Y., and Xiao, G., Beilstein J. Org. Chem., 2016, vol. 12, pp. 2443–2449.
GB Patent 807196, 1956.
US Patent 2757146, 1956.
US Patent 4675462, 1987.
BR 8605269, 1987.
Winberg, H.E. and Fawcett, F.S., Org. Synth., 1962, vol. 42, p. 83.
Chow, H.-F., Low, K.-H., and Wong, K.I., Synlett, 2005, no. 14, pp. 2130–2134.
Obshchyaya organicjeskaya khimiya (General Organic Chemistry) Kochetkov, N.K., Ed., Moscow: Khimiya, 1981, vol. 3, pp. 68–70.
US Patent 4532369, 1985.
US Patent 4795838, 1989.
US Patent 4806702, 1989.
US Patent 4734533, 1988.
US Patent 4769505, 1987.
US Patent 4816608, 1989.
US Patent 4853488, 1989.
US Patent 5110903, 1992.
Jpn. Patent 041146, 1992.
Wang, Z., Dong, F., Lu, J., Lui, J., and Ma, H., Chin. J. Org. Chem., 2001, vol. 21, no. 7, pp. 538–540.
Tao, N., Xiao, G., Tong, Y., and Niu, L., Fine Chem., 2009, vol. 26, no. 12, pp. 1159–1162.
CN Patent 105348029, 2015.
Long, Z., Juan, W., Leng, G., Yulun, X., and Weimin, G., Proc. SPIE, 2005, vol. 6029, pp. 1–6.
ChSSR Patent 247592, 1998.
RF Patent 2101272, 1998.
US Patent 4783561, 1988.
US Patent 4849559, 1989.
US Patent 5679874, 1997.
Jpn. Patent 074759, 1995.
Ito, Y., Miyata, S., Nakatsuka, M., and Saegusa, T., J. Org. Chem., 1981, vol. 46, no. 5, pp. 1043–1044.
Cram, D.J. and Steinberg, H., J. Am. Chem. Soc., 1951, vol. 73, no. 12, pp. 5691–5704.
Cram, D.J., Usp. Khim., 1960, vol. 29, no. 8, pp. 1029–1047.
Tacahashi, S. and Mori, N., Chem. Lett., 1989, vol. 18, no. 1, pp. 13–14.
Brown, G.W. and Sonheimer, F., J. Am. Chem. Soc., 1967, vol. 89, no. 26, pp. 7116–7117.
Kaplan, M.L. and Truesdale, E.A., Tetrahedron Lett., 1976, vol. 17, no. 41, pp. 3665–3666.
Boekelheide, V., Reingold, I.D., and Tuttle, M., J. Chem. Soc., Chem. Commun., 1973, pp. 406–407.
Vögtle, F., Fornell, P., and Löhr, W., Chem. Ind., 1979, p. 416.
Coray, A.R., J. Organomet. Chem., 1983, vol. 243, no. 2, pp. 191–193.
PL Patent 162243, 1990.
Higuchi, H., Kugimiya, M., Otsubo, T., Sakata, Y., and Misumi, S., Tetrahedron Lett., 1983, vol. 24, no. 25, pp. 2593–2594.
Higuchi, H., Tani, K., Otsubo, T., Sakata, Y., and Misumi, S., Bull. Chem. Soc. Jpn., 1987, vol. 60, no. 11, pp. 4027–4036.
Higuchi, H. and Misumi, S., Tetrahedron Lett., 1982, vol. 23, no. 52, pp. 5571–5574.
Higuchi, H., Otsubo, T., Ogura, F., Yamaguchi, H., Sakata, Y., and Misumi, S., Bull. Chem. Soc. Jpn., 1982, vol. 55, no. 1, pp. 182–187.
Takemura, H., Shinmyozu, T., and Inazu, T., Tetrahedron Lett., 1988, vol. 29, no. 9, pp. 1031–1032.
Isaji, H., Sako, K., Takemura, H., Tatemitsu, H., and Shinmyozi, T., Tetrahedron Lett., 1998, vol. 39, no. 24, pp. 4303–4304.
Isaji, H., Yasutake, M., Takemura, H., Sako, K., Tatemitsu, H., Inazu, T., and Shinmyozi, T., Eur. J. Org. Chem., 2001, vol. 2001, no. 13, pp. 2487–2499.
Kurosawa, K., Suenaga, M., Inazu, T., and Yoshino, T., Tetrahedron Lett., 1982, vol. 23, no. 50, pp. 5335–5338.
Shinmyom, T., Hirai, Y., and Inazu, T., J. Org. Chem., 1986, vol. 51, no. 9, pp. 1551–1555.
Szunerits, S., Utley, J.H.P., and Nielsen, M.F., J. Chem. Soc., Perkin Trans. 2, 2000, vol. 4, pp. 669–675.
US Patent 3616314, 1971.
Hopf, H., Angew. Chem., Int. Ed. Engl., 1972, vol. 11, no. 5, pp. 419–420.
US Patent 3221068, 1965.
Yeh, V.L. and Gorham, W.F., J. Org. Chem., 1969, vol. 34, no. 8, pp. 2366–2370.
Reich, H.J. and Cram, D.J., J. Am. Chem. Soc., 1969, vol. 91, no. 13, pp. 3527–3533.
ACKNOWLEDGMENTS
This work was performed as part of a budget project no. 17-117041710081-1 for the Boreskov Institute of Cata-lysis, Siberian Branch, Russian Academy of Sciences.
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Translated by E. Glushachenkova
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Gogin, L.L., Yushchenko, D.Y., Konev, V.N. et al. Ways of Synthesizing Dichloro-[2,2]-Paracyclophane: A Review. Catal. Ind. 11, 34–44 (2019). https://doi.org/10.1134/S2070050419010057
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DOI: https://doi.org/10.1134/S2070050419010057