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Kinetics of chloromethylation of benzo-1,4-dioxane

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The chloromethylation of benzo-1,4-dioxane in acetic acid in presence of SnCl4, SbCl3, ZnCl2, and SbCl5 catalysts was investigated. The activation energy of the process was found to be 19.6 kcal/mole. The reaction is zero order in chloride ion and first order in the Hammett acidity function. In excess HCl the reaction is described by a second-order equation. The relative activities of the methyl chlorides in the chloromethylation of benzo-1,4-dioxane were determined.

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Literature cited

  1. R. M. Elderfield, (editor), Heterocyclic Compounds, Vol. 6, Wiley (1957).

  2. V. Daukshas and É. Udrenaite, Khim. Geterotsikl. Soedin., No. 9, 1155 (1975).

    Google Scholar 

  3. Z. Bidlo and F. Vonaseh, Prumysl. Potravin., 9, 589 (1958).

    Google Scholar 

  4. I. Drabek, Chem. Zvesti, 10, 357 (1956).

    Google Scholar 

  5. F. Dallacker and J. Bloemen. Monatsh. Chem., 92, 640 (1961).

    Google Scholar 

  6. K. Hejno and Z. Arnold, Chem. Listy, 47, 601 (1953).

    Google Scholar 

  7. I. R. Greigy, British Patent No. 566732; Chem. Abstr., 41, 1250 (1947).

    Google Scholar 

  8. V. Daukshas and P. Kadzyauskas, Nauchn. Tr. Vyssh. Uchebn. Lit. SSR, Ser. Khim., 3, 51 (1963).

    Google Scholar 

  9. J. Ogata and M. Okano, J. Am. Chem. Soc., 75, 5423 (1956).

    Google Scholar 

  10. A. I. Gel'bshtein, G. G. Shcheglova, and M. I. Temkin, Dokl. Akad. Nauk SSSR, 107, 108 (1956).

    Google Scholar 

  11. N. M. Émanuél' and D. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1962), p. 50.

  12. K. Laidler, Kinetics of Organic Reactions [Russian translation], Mir, Moscow (1966), p. 341.

    Google Scholar 

  13. A. Sh. Shatenshtein, Isotope Exchange and Hydrogen Substitution in Organic Compounds [in Russian], Izd. Akad. Nauk SSSR, Moscow (1960), p. 63.

    Google Scholar 

  14. C. Kelley and P. McCusker, J. Am. Chem. Soc., 65, 1307 (1943).

    Google Scholar 

  15. J. Lewis, J. R. Millee, R. L. Richards, and A. Thompson, J. Am. Chem. Soc., 11, 5850 (1965).

    Google Scholar 

  16. A. E. Agronomov and Yu. S. Shabarov, Laboratory Work in a Practical Organic Course [in Russian], Khimiya, Moscow (1974), p. 63.

    Google Scholar 

  17. J. Walker, Formaldehyde, Reinhold (1953).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 459–462, April, 1981.

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Lyushin, M.M., Bakus, P.Y. & Nagiev, A.I. Kinetics of chloromethylation of benzo-1,4-dioxane. Chem Heterocycl Compd 17, 324–328 (1981). https://doi.org/10.1007/BF00503326

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  • DOI: https://doi.org/10.1007/BF00503326

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