Abstract
It is shown by means of IR and PMR spectra that the products of the aminolysis of esters of 3,3-dimethyl(2-carbethoxy)levulinic acid and γ-chloro-β,β,γ-trimethylbutyrolactone exist in the cyclic form of 2-hydroxy-5-pyrrolidones (Ia-d). It was established by PMR spectroscopy that, except for the 4-carbamido derivative (Id), these compounds undergo spontaneous dehydration in anhydrous solutions. In addition, ring-chain tautomeric equilibrium is established in solutions of the N-phenyl derivative (Ib). The rates of establishment of equilibrium and the equilibrium positions were investigated for both processes.
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B. M. Sheiman, L. Ya. Denisova, S. F. Dymova, I. M. Kustanovich, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., 1190 (1971).
P. R. Jones, Chem. Rev., 63, 471 (1963).
W. Flitsh, Chem. Ber., 103, 3205 (1970).
R. Lukes and Z. Linhartova, Coll. Czech. Chem. Commun., 25, 502 (1960).
D. Hammond, in; Steric Effects in Organic Chemistry, M. S. Newman (editor), Wiley (1956).
B. V. Unkovskii, L. A. Ignatova, and M. G. Zaitseva, Khim. Geterotsikl. Soedin., 889 (1969).
I. Finkelstein, T. Willams, V. Toome, and S. Traiman, J. Org. Chem., 32, 3229 (1967).
B. M. Sheiman, L. Ya. Denisova, S. F. Dymova, I. M. Kustanovich, and V. M. Berezovskii, Zh. Organ. Khim., 5, 238 (1969).
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See [1] for communication VIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 22–26, January, 1973.
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Sheiman, B.M., Denisova, L.Y., Dymova, S.F. et al. Syntheses of di- and tetrahydropyrroles. Chem Heterocycl Compd 9, 18–21 (1973). https://doi.org/10.1007/BF00476140
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DOI: https://doi.org/10.1007/BF00476140