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Functional Methacryloyloxy Acetals: V. Electrophilic Addition of Carboxylic Acids to 2-Vinyloxyethyl Methacrylate

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Abstract

Mono- and dicarboxylic acids (acetic, methacrylic, E-crotonic, and malonic) quantitatively add to 2-vinyloxyethyl methacrylate under mild conditions (1 wt % CF3COOH, 20–60°C, 1–4 h) according to the Markownikoff rule to give the corresponding mono- and bis-adducts with high regio- and chemoselectivity. The products may be regarded as a new family of functionalized methacrylates.

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REFERENCES

  1. Vysotskaya, O.V., Oparina, L.A., Parshina, L.N., Gusarova, N.K., and Trofimov, B.A., Russ. J. Org. Chem., 2003, vol. 39, p. 585.

    Google Scholar 

  2. Mikhaleva, A.I. and Gusarova, N.K., Atsetilen: reaktsii i proizvodnye (Acetylene: Reactions and Derivatives), Novosibirsk: Sibirsk. Otd. Ross. Akad. Nauk, 1999.

    Google Scholar 

  3. Trofimov, B.A., Lavrov, V.I., Alekankin, V.N., Stankevich, V.K., Maksimov, S.M., Grigorenko, V.I., Petrov, G.N., Rappoport, L.Ya., and Parshina, L.N., USSR Inventor's Certificate no. 771 084, 1978; Byull. Izobret., 1980, no. 38.

  4. Trofimov, B.A., Lavrov, V.I., Parshina, L.N., Alekankin, V.N., Stankevich, V.K., and Grigorenko, V.I., Zh. Org. Khim., 1982, vol. 18, p. 528.

    Google Scholar 

  5. Andrei, M., Marchese, L., Roggero, A., and Ferrari, M., US Patent no. 5 264 307, 1993; Chem. Abstr., 1994, vol. 120, no. 147 220 b.

  6. Gorelova, O.V., Oparina, L.A., Parshina, L.N., Gusarova, N.K., and Trofimov, B.A., Russ. J. Org. Chem., 2001, vol. 37, p. 1683.

    Google Scholar 

  7. Vysotskaya, O.V., Oparina, L.A., Parshina, L.N., Gusarova, N.K., and Trofimov, B.A., Russ. J. Org. Chem., 2002, vol. 38, p. 1082.

    Google Scholar 

  8. Oparina, G.A., Vysotskaya, O.V., Parshina, L.N., Gusarova, N.K., and Trofimov, V.A., Phosphorus, Sulfur, Silicon Relat. Elem., 2003, in press.

  9. Annenkov, V.V., Danilovtseva, E.N., Vysotskaya, O.V., Oparina, L.A., Mikhaleva, A.I., and Trofimov, B.A., Vysokomol. Soedin., Ser. B, 2002, p. 2241.

  10. Vysotskaya, O.V., Cand. Sci. (Chem.) Dissertation, Irkutsk, 2002.

  11. Vysotskaya, O.V., Oparina, L.A., Parshina, L.N., Gusarova, N.K., and Trofimov, B.A., Abstracts of Papers, XV Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimii” (XVth Int. Scientific-Technical Conf. “Chemical Reagents and Small-Scale Chemical Processes”), Ufa, 2002, p. 7.

  12. Trofimov, B.A., Vysotskaya, O.V., Oparina, L.A., Parshina, L.N., and Gusarova, N.K., Nauka Proizvod., 2003, no. 6, p. 16.

  13. Trofimov, B.A., Heteroatomnye proizvodnye atsetilena. Novye monomery, reagenty i poluprodukty (Heteroatom Acetylene Derivatives. New Monomers, Reagents, and Intermediate Products), Moscow: Nauka, 1981.

    Google Scholar 

  14. Trofimov, V.A. and Nedolya, N.A., Rev. Heteroatom Chem., 1993, vol. 9, p. 205.

    Google Scholar 

  15. Nedolya, N.A., Khil'ko, M.Ya., and Trofimov, B.A., Zh. Org. Khim., 1987, vol. 23, p. 1181.

    Google Scholar 

  16. Nedolya, N.A., Zinov'eva, V.P., and Trofimov, B.A., Zh. Org. Khim., 1989, vol. 25, p. 2759.

    Google Scholar 

  17. Nedolya, N.A., Zinov'eva, V.P., Tatarova, T.F., and Trofimov, B.A., Zh. Org. Khim., 1989, vol. 25, p. 2271.

    Google Scholar 

  18. Nedolya, N.A., Papsheva, N.P., Sarapulova, G.I., Afonin, A.V., and Trofimov, B.A., Zh. Org. Khim., 1991, vol. 27, p. 2060.

    Google Scholar 

  19. Nedolya, N.A., Tolmachev, S.V., and Zinov'eva, V.P., Russ. J. Org. Chem., 2001, vol. 37, p. 1074.

    Google Scholar 

  20. Nedolya, N.A., Shlyakhtina, N.I., Zinov'eva, V.P., Dmitrieva, L.L., and Sarapulova, G.I., Russ. J. Gen. Chem., 2002, vol. 72, p. 760.

    Google Scholar 

  21. Shostakovskii, M.F., Prostye vinilovye efiry (Vinyl Ethers), Moscow: Akad. Nauk SSSR, 1952.

    Google Scholar 

  22. Mikhant'ev, B.I., Mikhant'ev, V.B., Lapenko, V.L., and Voinova, V.K., Nekotorye vinil'nye monomery (Some Vinyl Monomers), Voronezh: Voronezh. Gos. Univ., 1970, p. 60.

    Google Scholar 

  23. Gusarova, N.K., Ivanova, N.I., Reutskaya, A.M., Arbuzova, S.N., and Trofimov, B.A., Russ. J. Gen. Chem., 1999, vol. 69, p. 1839.

    Google Scholar 

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,ul. Favorskogo 1, Irkutsk, 664033, Russia

    O. V. Vysotskaya, L. A. Oparina, L. N. Parshina, A. A. Tatarinova & B. A. Trofimov

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  1. O. V. Vysotskaya
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  2. L. A. Oparina
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  3. L. N. Parshina
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  4. A. A. Tatarinova
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  5. B. A. Trofimov
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Vysotskaya, O.V., Oparina, L.A., Parshina, L.N. et al. Functional Methacryloyloxy Acetals: V. Electrophilic Addition of Carboxylic Acids to 2-Vinyloxyethyl Methacrylate. Russian Journal of Organic Chemistry 40, 307–310 (2004). https://doi.org/10.1023/B:RUJO.0000034962.38627.eb

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  • DOI: https://doi.org/10.1023/B:RUJO.0000034962.38627.eb

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