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Aziridinyl ketones and their heteroanalogs. 5. Synthesis and structures of 2-aryl-3-aroylaziridines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of trans- and cis-isomeric 1-R-2-aryl-3-aroylaziridines were synthesized, and their IR spectra were studied. Intramolecular hydrogen bonding is realized in the trans isomers when R = H, and they exist in the only possible conformation (intermediate between a gauche and a cisoid conformation). cis-Isomers II (R = alkyl) exist in solutions in the form of two conformers, viz., gauche and cisoid conformers, and the gauche conformer is thermodynamically preferable.

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Literature cited

  1. V. D. Orlov, F. G. Yaremenko, N. N. Kolos, N. S. Pivnenko, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., No. 4, 544 (1980).

    Google Scholar 

  2. N. H. Cromwell, Lect. Heterocycl. Chem., 3, (1976).

  3. N. H. Cromwell, Chem. Rev., 38, 83 (1946).

    Google Scholar 

  4. P. L. Soutwick and R. J. Shozda, J. Am. Chem. Soc., 82., 2888 (1960).

    Google Scholar 

  5. E. P. Styngach and A. A. Semenov, Izv. Akad. Nauk Moldavsk. SSR, Ser. Biol. Khim. Nauk, 62 (1975).

  6. R. G. Kostyanovskii, V. F. Rudchenko, A. V. Prosyanik, M. D. Isobaev, I. I. Chervin, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., 628 (1977).

  7. P. Tarburton, P. B. Woller, R. C. Badger, E. Doomes, and N. H. Cromwell, J. Heterocycl. Chem., 14, 459 (1977).

    Google Scholar 

  8. R. Martine, A. Secoches, A. Lattes, and R. Mathis-Noel, Compt. Rend., Ser. B, 270, 154 (1970).

    Google Scholar 

  9. V. D. Orlov, F. G. Yaremenko, Yu. N. Surov, and V. F. Lavrushin, Dokl. Akad. Nauk Ukr. SSR, Ser. B, No. 11, 932 (1979).

    Google Scholar 

  10. N. H. Cromwell, R. E. Bambury, and J. I. Adelfang, J. Am. Chem. Soc., 82, 4241 (1960).

    Google Scholar 

  11. P. Tarburton, L. J. Wolpa, R. K. Loerch, T. L. Folsom, and N. H. Cromwell, J. Heterocycl. Chem., 14, 1203 (1977).

    Google Scholar 

  12. V. D. Orlov, S. A. Korotkov, Yu. A. Sukach, and V. F. Lavrushin, Zh. Obshch. Khim., 43, 1353 (1973).

    Google Scholar 

  13. V. G. Orville-Thomas, The Internal Rotation in Molecules, Wiley-Interscience (1974).

  14. V. D. Orlov, F. G. Yaremenko, Yu. N. Surov, and V. F. Lavrushin, Zh. Obshch. Khim., 49, 2602 (1979).

    Google Scholar 

  15. F. G. Weber and C. Bandlow, Z. Chem., 13, 467 (1973).

    Google Scholar 

  16. N. H. Cromwell, N. Barker, R. Wankel, P. Vanderhorst, F. Olson, and J. H. Anglin, J. Amer. Chem. Soc., 73, 1044 (1951).

    Google Scholar 

  17. G. Drefahl, K. Ponsold, and B. Schonecker, Ber., 97, 2014 (1964).

    Google Scholar 

  18. H. W. Heine, R. H. Weese, R. A. Cooper, and A. J. Durbetaki, J. Org. Chem., 32, 2708 (1967).

    Google Scholar 

  19. T. DoMinh and A. M. Trozzolo, J. Am. Chem. Soc., 94, 4046 (1972).

    Google Scholar 

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See [1] for Communication A.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 11, pp. 1489–1494, November, 1980.

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Orlov, V.D., Yaremenko, F.G. & Lavrushin, V.F. Aziridinyl ketones and their heteroanalogs. 5. Synthesis and structures of 2-aryl-3-aroylaziridines. Chem Heterocycl Compd 16, 1128–1133 (1980). https://doi.org/10.1007/BF00504108

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