Abstract
The 2- and 3-tert-butylderivatives of 1-methylpyrrole, hitherto unknown, have been obtained by a single-stage method. The process is characterized by a low positional selectivity with asomewhat predonminating β-substitution. The results have been compared with data, obtained by the quantum-chemical calculation of the molecules of pyrrole, N-methylpyrrole, and also of their σ-complexes with protons, introduced in the α- and β-position of the rings.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E. Ya. Lukevits, L. M. Ignatovich, Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 853 (1986).
I. G. Iovel', Yu. Sh. Gol'dberg, M. V. Shimanskaya, and E. Lukevits, Synth. Commun.,18, 1261 (1988).
I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskya, J. Mol. Catal.,57, 91 (1989).
I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 746 (1989).
I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 12, 1640 (1991).
P. S. Skel and G. P. Bean, J. Am. Chem. Soc.,84, 4655 (1962).
P. B. Gerritt, J. Org. Chem.,32, 229 (1967).
R. Nicoletti and C. Germani, Ricerca Sci.,36, 1343 (1966).
J. K. Groves, H. J. Anderson, and H. Nagy, Cand. J. Chem.,49, 2427 (1971).
R. A. Jones and G. P. Bean, The Chemistry of Pyrroles, Acad. Press, New York (1977).
A. F. Pozharskii, Theoretical Foundations of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).
E. Pretsch, T. Clerc, J. Seibl, and W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds. Chemical Laboratory Practical, 2nd Ed., Springer-Verlag, Berlin (1989).
A. H. Jackson, D. Barton, and N. D. Ollis (eds.), Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds, Vol. 4, Pergamon Press, Oxford (1979), p. 275.
J. A. Pople and D. L. Beveridge, Approximate Molecular Orbital Theory, McGraw Hill, New York (1970), p. 236.
V. I. Ivanskii, The Chemistry of Heterocyclic Compounds [in Russian], Vysshaya Shkola, Moscwo (1978).
D. Rinaldi, GEOMO Program System N 290. Quantum Chemistry Program Exchange, Indiana University, Bloomington (1975).
G. D. Andreetti, G. Bocelli, L. Cavalca, and P. Sgarabotto, Gazz. Chim. Ital.,104, 331 (1974).
Additional information
Latvian Institute of Organic Synthesis, Riga LV-1006.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 163–167, February, 1995. Original article submitted January 17, 1995.
Rights and permissions
About this article
Cite this article
Iovel', I., Fleisher, M., Popelis, Y. et al. Alkylation of n-methylpyrrole with tert-butanol in the presence of amberlyst 15 ion exchanger. Chem Heterocycl Compd 31, 140–143 (1995). https://doi.org/10.1007/BF01169667
Issue Date:
DOI: https://doi.org/10.1007/BF01169667