Pyrroloindoles. 8. Electrophilic substitution in the 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole series
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The principles of the electron density distribution in 1H,5H-pyrrolo [2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole molecules were determined on the basis of quantumchemical calculations. These results were confirmed by the results of the investigated electrophilic-substitution reactions. The reaction centers of these compounds proved to be the same positions as in indole, viz., the 3 and 7 and 1 and 8 positions, respectively. The impossibility of 1,8-disubstitution in the angular heteroring was demonstrated in the case of bulky substituents; this was explained by a steric effect.
KeywordsOrganic Chemistry Reaction Center Indole Density Distribution Steric Effect
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- 1.S. V. Dolidze, Sh. A. Samsoniya, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 5, 608 (1983).Google Scholar
- 2.V. G. Maslov, Zh. Strukt. Khim., 18, 414 (1977).Google Scholar
- 3.O. A. Yuzhakova, L. N. Kurkovskaya, N. N. Shapet'ko, V. K. Potapov, and A. I. Shatenshtein, Teor. Éksp. Khim., 7, 962 (1971).Google Scholar
- 4.Organic Syntheses [Russian translation], Collective Vol. 11, Inostr. Lit., Moscow (1949), p. 30.Google Scholar
- 5.G. Kinast and L. F. Tietze, Angew. Chem., 88, 261 (1976).Google Scholar
- 6.J. E. Saxton, J. Chem. Soc., No. 9, 3592 (1952).Google Scholar
- 7.V. G. Avramenko, V. D. Nazina, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 8, 1071 (1970).Google Scholar