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Conformational analysis of carbonyl derivatives of 1,3,3-trimethyl-2-methyleneindoline

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The preferred conformations of a number of carbonyl derivatives of 1,3,3-trimethyl-2-methyleneindoline were determined by PMR spectroscopy with the use of lanthanide shift reagents. It was established that the COR group is trans-oriented relative to the heteroring nitrogen atom, and the aldehyde exists primarily in the s-trans conformation, and the ketones exist primarily in the s-cis conformation. The conclusions regarding the structures of the preferred conformations of the investigated compounds were confirmed by data from the IR spectra.

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Literature cited

  1. E. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill (1962).

  2. M. Yu. Kornilov and A. V. Turov, Khim. Geterotsikl. Soedin., No. 10, 1299 (1979).

    Google Scholar 

  3. M. Yu. Kornilov, E. D. Matveeva, V. A. Budylin, L. G. Yudin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 1, 139 (1973).

    Google Scholar 

  4. R. Radeglia and A. Weber, J. Prakt. Chem., 314, 884 (1972).

    Google Scholar 

  5. F. S. Babichev, Nauk. Zap. KDU, Khim. Zb., No. 7, 206 (1956).

    Google Scholar 

  6. M. Yu. Kornilov, A. V. Turov, and V. I. Zamkovoi, Ukr. Khim. Zh., 41, 769 (1975).

    Google Scholar 

  7. H. M. McConnell and R. E. Robertson, J. Chem. Phys., 29, 1361 (1958).

    Google Scholar 

  8. M. Yu. Kornilov, F. S. Babichev, V. I. Zamkovoi, A. N. Kost, G. P. Kutrov, E. D. Matveeva, A. M. Nesterenko, A. V. Turov, A. K. Tyltin, L. G. Yudin, and N. S. Yaremchuk, in: Application of Conformational Analysis in the Synthesis of New Organic Substances. Material from the Republican Conference on Dynamic Stereochemistry and Conformational Analysis [in Russian], Odessa (1975), p. 29.

  9. N. H. Cromwell, F. A. Miller, A. R. Johnson, R. L. Frank, and D. J. Wallace, J. Am. Chem. Soc., 71, 3337 (1949).

    Google Scholar 

  10. G. Montaudo, V. Librando, S. Caccamese, and P. Maravigna, J. Am. Chem. Soc., 95, 6365 (1973).

    Google Scholar 

  11. French Patent No. 829442; Compt. Rend., 1, 808 (1939).

  12. H. Fritz, Chem. Ber., 92, 1809 (1959).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 361–364, March, 1983.

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Zemlyanoi, V.N., Mushkalo, I.L., Kornilov, M.Y. et al. Conformational analysis of carbonyl derivatives of 1,3,3-trimethyl-2-methyleneindoline. Chem Heterocycl Compd 19, 293–296 (1983). https://doi.org/10.1007/BF00513263

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  • DOI: https://doi.org/10.1007/BF00513263

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