Abstract
The catalytic activity of alkali metal hydroxides in base-catalyzed addition of 1-heptanol to acetylene depends on the alkali metal nature and degree of hydration of its hydroxide. In a closed system, the catalytic activity of alkali metal hydroxides decreases in the series 2KOH·H2O > RbOH·H2O > CsOH·H2O > NaOH. The corresponding series for a flow system is as follows: RbOH·H2O > CsOH·H2O > 2KOH·H2O > NaON > KOH·H2O. The difference is explained by participation of the catalyst in side reactions with both 1-heptanol and acetylene. Addition of dimethyl sulfoxide to the catalytic system accelerates the vinylation process.
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REFERENCES
Parshina, L.N., Sokolyanskaya, L.V., Nosyreva, V.V., Scotheim, T., Zefirov, N.S., and Trofimov, B.A., Russ. J. Org. Chem., 1999, vol. 35, no. 2, pp. 202-206.
Akademik Aleksei Evgrafovich Favorskii. Izbrannye trudy (Academician Aleksei Evgrafovich Favorskii. Selected Papers), Moscow: Akad. Nauk SSSR, 1961.
Shostakovskii, M.F., Prostye vinilovye efiry (Vinyl Ethers), Moscow: Akad. Nauk SSSR, 1952.
Reppe, W., Justus Liebigs Ann. Chem., 1956, vol. 601, pp. 81-138.
Kopenhaver, J. and Bigelou, M., The Chemistry of Acetylene and Related Compounds, Bergmann, E.D., Ed., New York: Intersci., 1948. Translated under the title Khimiya atsetilena, Moscow: Inostrannaya Literatura, 1954, pp. 174-239.
Shostakovskii, M.F., Trofimov, B.A., Atavin, A.S., and Lavrov, V.I., Usp. Khim., 1968, vol. 37, pp. 2070-2093.
Trofimov, B.A., Geteroatomnye proizvodnye atsetilena. Novye polifunktsional'nye monomery, reagenty i poluprodukty (Heteroatomic Acetylene Derivatives. New Polyfunctional Monomers, Reagents, and Intermediate Products), Moscow: Nauka, 1981.
Tedeschi, R.J., Encyclopedia of Physical Science and Technology, New York: Academic, 1992, vol. 1, pp. 27-65.
Miller, S.A., Acetylene, Its Properties, Manufacture, and Uses, London: Benn, 1966, vol. 2, pp. 198-245.
Miller, S.I. and Shkapenko, G., J. Am. Chem. Soc., 1955, vol. 77, no. 19, pp. 5038-5041.
Nagasawa, F. and Matsuzawa, K., J. Chem. Soc. Jpn., Ind. Chem. Sec., 1958, vol. 61, no. 1, pp. 28-33.
Otsuka, S., Matsui, Y., and Murahashi, S., Nippon Kagaku Zasshi, 1956, vol. 77, no. 5, pp. 766-773.
Otsuka, S., Matsui, Y., and Murahashi, S., Nippon Kagaku Zasshi, 1959, vol. 80, no. 10, pp. 1157-1160.
US Patent no. 1 866 328, 1932; Chem. Abstr., 1932, vol. 26, no. 16, p. 4345.
US Patent no. 1 866 329, 1932; Chem. Abstr., 1932, vol. 26, no. 16, p. 4345.
US Patent no. 1 866 430, 1932; Chem. Abstr., 1932, vol. 26, no. 16, p. 4345.
Steinborn, D., Mosinski, H., and Rosenstock, T., J. Organomet. Chem., 1991, vol. 414, pp. 45-50.
Widon, B., Technique of Organic Chemistry, Weissberger, A., Ed., New York: Intersci., 1965, 3rd ed., vol. 11, part 2. Translated under the title Metody organicheskoi khimii. Ustanovlenie struktury organicheskikh soedinenii fizicheskimi i khimicheskimi metodami, Moscow: Khimiya, 1967, vol. XI, part II, pp. 234-290.
Trofimov, B.A., Usp. Khim., 1981, vol. 50, pp. 248-272.
Trofimov, B.A., Z. Chem., 1986, vol. 26, no. 2, pp. 41-49.
Trofimov, B.A., Zh. Org. Khim., 1986, vol. 22, no. 9, pp. 1991-2006.
Trofimov, B.A., Russ. J. Org. Chem., 1995, vol. 31, no. 9, pp. 1233-1252.
Steinborn, D., Rosenstock, T., and Sieler, J., J. Prakt. Chem., 1996, vol. 338, no. 3, pp. 264-269.
Trofimov, B.A., Oparina, L.A., Lavrov, V.I., and Parshina, L.N., Russ. J. Org. Chem., 1995, vol. 31, no. 5, pp. 597-600.
Miller, S.A., Acetylene, Its Properties, Manufacture, and Uses, London: Benn, 1966, vol. 1. Translated under the title Atsetilen, ego svoistva, poluchenie i primenenie, Leningrad: Khimiya, 1969, vol. 1, pp. 308-310.
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Parshina, L.N., Oparina, L.A., Gorelova, O.V. et al. Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: X. Catalytic Effect of Alkali Metal Hydroxides in the Vinylation of 1-Heptanol. Russian Journal of Organic Chemistry 37, 940–945 (2001). https://doi.org/10.1023/A:1012462113437
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DOI: https://doi.org/10.1023/A:1012462113437