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.
Similar content being viewed by others
Literature cited
T. É. Bezmenova, R. A. Dorofeeva, and A. Ya. Bezmenov, Zh. Org. Khim., 3, 778 (1967).
T. É. Bezmenova, D. I. Kurlyand, A. F. Rekasheva, T. D. Zaika, and T. S. Lutsii, Khim. Geterotsikl. Soedin., No. 8, 1067 (1975).
T. É. Bezmenova, A. F. Rekasheva, T. S. Lutsii, and R. A. Dorofeeva, Khim. Geterotsikl. Soedin., No. 9, 1200 (1974).
Takanashi, L. A. Cohen, H. K. Miller, and E. L. Peake, J. Org. Chem., 36, 1205 (1971).
T. J. Crowell, R. T. Kemp, R. E. Lutz, A. A. Wall, J. Am. Chem. Soc., 90, 4638 (1968).
L. R. Fedor and W. R. Clave, J. Am. Chem. Soc., 93, 985 (1971).
B. Loev, J. Org. Chem., 26., 4394 (1961).
H. S. Harned and L. D. Fallon, J. Am. Chem. Soc., 61, 2374 (1939).
N. M. Émanuel' and I. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1969), p. 157.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1188–1191, September, 1976.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00480387