Abstract
The selectivity of the position of nitration of 1-methylpyrrole, 1,2-dimethylpyrrole, 1,2-dihydropyrrolizine, and 5,6,7,8-tetrahydropyrrocoline was found. In contrast to the selectivity of substitution during nitration of their carbocyclic analogs, o-xylene, indane and tetraline, the fraction of the α-nitro-isomer in the nitration products of 1,2-dimethylpyrrole is smaller than the fraction of α-nitro derivatives of 1,2-dihydropyrrolizine and 5,6,7,8-tetrahydropyrrocoline, and in the two latter cases the isomers are almost equally distributed. During nitration of the above bicyclic pyrroles, the Mills-Nixon effect does not appreciably influence the selectivity of the position of the reaction.
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Literature Cited
L. N. Astakhova, I. M. Skvortsov, L. V. Safonova, and V. I. Makukhina, Khim. Geterotsikl. Soedin., No. 3, 320 (1986).
H. J. Anderson, Can. J. Chem., 35, 21 (1957).
A. R. Cooksey, K. J. Morgan, and D. P. Morrey, Tetrahedron, 26, 5101 (1970).
P. E. Sonnet, J. Heterocycl. Chem., 7, 399 (1970).
G, Doddi, P. Mencarelli, A. Razzini, and F. Stegel, J. Org. Chem., 44, 2321 (1979).
L. Grehn, Chem. Scr., 13, 67 (1978–1979).
L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 12, 1587 (1979).
J. Vaughan, G. J. Welch, and G. J. Wright, Tetrahedron, 21, 1665 (1965).
J. M. Patterson, J. Brasch, and P. Drenchko, J. Org. Chem., 26, 4712 (1961).
G. M. Badger, Q. Rev., 5, 147 (1951).
P. J. Garratt and D. N. Nicolaides, J. Org. Chem., 39, 2222 (1974).
R. J. Taylor, J. Chem. Soc. B, No. 12, 1559 (1968).
F. P. Doyle, M. D. Mehta, G. S. Sach, and J. L. Pearson, J. Chem. Soc., No. 12, 4458 (1958).
I. P. Skvortsov, N. A. Buntyakova, A. A. Stolyarchuk, and N. I. Ivanova, Khim.-Farm. Zh., No. 5, 66 (1977).
J. M. Patterson, J. Brasch, and P. Drenchko, J. Org. Chem., 27, 1652 (1962).
I. M. Skvortsov and I. V. Antipova, Khim. Geterotsikl. Soedin., No. 6, 764 (1978).
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See [1] for Communication 23.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1489–1491, November, 1987.
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Skvortsov, I.M., Astakhova, L.N. 1-Azabicyclic compounds. 24. Selectivity of position of nitration of 1,2-dihydropyrrolizine, 5,6,7,8-tetrahydropyrrocoline and pyrrole homologs. Chem Heterocycl Compd 23, 1189–1191 (1987). https://doi.org/10.1007/BF00479366
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DOI: https://doi.org/10.1007/BF00479366