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Reaction of 3-AR(ALK)oxysulfolanes with amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

On the basis of data on the kinetics of the hydrolysis of 3-aroxysulfolanes in aqueous solutions of tertiary amines and in acetonitrile it is shown that the elimination of phenols is subject to specific base catalysis and occurs via an (ElcB)R carbanion mechanism. The exchange of aroxy and alkoxy groups of sulfolanyl ethers on reaction with nucleophilic reagents is explained by an elimination-addition scheme.

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Literature cited

  1. T. É. Bezmenova, R. A. Dorofeeva, and A. Ya. Bezmenov, Zh. Org. Khim., 3, 778 (1967).

    Google Scholar 

  2. T. É. Bezmenova, D. I. Kurlyand, A. F. Rekasheva, T. D. Zaika, and T. S. Lutsii, Khim. Geterotsikl. Soedin., No. 8, 1067 (1975).

    Google Scholar 

  3. T. É. Bezmenova, A. F. Rekasheva, T. S. Lutsii, and R. A. Dorofeeva, Khim. Geterotsikl. Soedin., No. 9, 1200 (1974).

    Google Scholar 

  4. Takanashi, L. A. Cohen, H. K. Miller, and E. L. Peake, J. Org. Chem., 36, 1205 (1971).

    Google Scholar 

  5. T. J. Crowell, R. T. Kemp, R. E. Lutz, A. A. Wall, J. Am. Chem. Soc., 90, 4638 (1968).

    Google Scholar 

  6. L. R. Fedor and W. R. Clave, J. Am. Chem. Soc., 93, 985 (1971).

    Google Scholar 

  7. B. Loev, J. Org. Chem., 26., 4394 (1961).

    Google Scholar 

  8. H. S. Harned and L. D. Fallon, J. Am. Chem. Soc., 61, 2374 (1939).

    Google Scholar 

  9. N. M. Émanuel' and I. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1969), p. 157.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1188–1191, September, 1976.

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Bezmenova, T.É., Tantsyura, V.P., Dorofeeva, R.A. et al. Reaction of 3-AR(ALK)oxysulfolanes with amines. Chem Heterocycl Compd 12, 983–986 (1976). https://doi.org/10.1007/BF00480387

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  • DOI: https://doi.org/10.1007/BF00480387

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