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Kinetics and mechanism of the reaction of 5-bromo-2- carbonyl derivatives of furan with amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The kinetics of exchange of bromine in 5-bromo-2-carbonyl derivatives of furan by dimethylamino and morpholino groups was studied. The reaction is kinetically complicated for 5-bromofurfural (I) — aldehyde I initially reacts simultaneously at both the carbonyl group to give the aminocarbinol and at the bromine atom with exchange by an amino group. The accumulation of the ammonium salt in the latter reaction leads to the development of an autocatalytic reaction, the product of which is 5-N,N-dialkylaminofurfurylidene-N,N-dialkylammonium bromide. Amines react with the ketones without complications; the second-order rate constants are presented. The rate of exchange decreases in the order CHO > COC6H5 > COCH=CHC6H5 > COCH3 > CH=CHCOC6H5.

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Literature cited

  1. L. P. Hammett, Physical Organic Chemistry, McGraw-Hill (1970).

  2. W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw-Hill (1969).

  3. M. O. Lidak and S. A. Giller, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 49 (1961).

  4. L. Do Amaral, J. Org. Chem., 37, 1433 (1972).

    Google Scholar 

  5. J. Miller, J. Amer. Chem. Soc., 76, 448 (1954).

    Google Scholar 

  6. H. Bader, A. R. Hansen, and F. J. McCarty, J. Org. Chem., 31, 2319 (1966).

    Google Scholar 

  7. P. L. Noyak and K. K. Satpathy, J. Indian Chem. Soc., 49, 615 (1972).

    Google Scholar 

  8. V. N. Novikov, Z. N. Nazarova, L. D. Babeshkina, and T. F. Mikhailova, Summary of Papers on the Mechanisms of Heterolytic Reactions [in Russian], Leningrad (1974), p. 53.

  9. V. N. Novikov and Z. N. Nazarova, Khim. Geterotsikl. Soedin., No. 1, 3 (1967).

    Google Scholar 

  10. Z. N. Nazarova and L. D. Babeshkina, Zh. Organ. Khim., 2, 1903 (1966).

    Google Scholar 

  11. Z. N. Nazarova and L. D. Babeshkina, Zh. Organ. Khim., 4, 176 (1968).

    Google Scholar 

  12. V. N. Novikov, V. Ts. Bukhaeva, F. T. Pozharskii, and A. M. Simonov, Khim. Geterotsikl. Soedin.. No. 2, 252 (1971).

    Google Scholar 

  13. Z. N. Nazarova, Zh. Obshch. Khim., 575 (1954).

  14. Z. N. Nazarova, Yu. A. Babaev, and G. N. Natal'ina, Zh. Obshch. Khim., 1431 (1963).

  15. R. Grigg, I. A. Knight, and M. V. Sargent, J. Chem. Soc., 6057 (1963).

  16. Z. N. Nazarova and A. D. Garnovskii, Zh. Obshch. Khim., 1182 (1960).

  17. Z. N. Nazarova, V. N. Novikov, and V. S. Pustovarov, Zh. Organ. Khim., 2, 161 (1966).

    Google Scholar 

  18. Experimental Methods in Chemical Kinetics [in Russian], Moscow (1971). p. 28.

  19. K. J. Laidler, Kinetics of Organic Reactions [Russian translation], Mir, Moscow (1966).

    Google Scholar 

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Authors and Affiliations

  1. Rostov State University, Rostov-on-Don

    V. N. Novikov & L. D. Babeshkina

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  1. V. N. Novikov
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  2. L. D. Babeshkina
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1465–1470, November, 1976.

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Novikov, V.N., Babeshkina, L.D. Kinetics and mechanism of the reaction of 5-bromo-2- carbonyl derivatives of furan with amines. Chem Heterocycl Compd 12, 1208–1212 (1976). https://doi.org/10.1007/BF00470214

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  • DOI: https://doi.org/10.1007/BF00470214

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