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2-Carbamoylaziridine (Leakadine): diastereoselective transformations and stereoelectronic effect*

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Chemistry of Heterocyclic Compounds Aims and scope

Diastereoselective transformations of Leakadine were discovered: dimerization during melting or heating in CHCl3 with the formation of one diastereomer. The obtained dimer reacts with methyl isocyanate under mild conditions with the formation of an N-methylcarbamoyl derivative – also in the form of one diastereomer. In the diastereoselective reaction of Leakadine with dimethyl formamide dimethyl acetal, 2-dimethylamino-1,3-diazabicyclo[3.1.0]hexan-4-one was obtained. The reaction of Leakadine with perfluoroisobutylene was studied.

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References

  1. I. Ya. Kalvin’sh and E. B. Astapenok, Belg. Pat. Appl. 860239; Chem. Abstr., 90, 34103j (1979).

  2. I. Ya. Kalvin’sh, N. M. Gipsh, A. G. Merson, E. B. Astapenok, and P. Trapencieris, USSR Inventor’s Certificate No. 787994; Byul. Izobret., No. 46, 214 (1980).

  3. O. Mitsunobu, Synthesis, 1 (1981).

  4. R. G. Kostyanovsky, P. E. Dormov, P. Trapencieris, B. Strumfs, G. K. Kadorkina, I. I. Chervin, and I. Ya. Kalvin’s, Mendeleev Commun., 9, 26 (1999).

    Article  Google Scholar 

  5. A. Kunath, F. Theil, and K. Jähnisch, J. Chromatogr., A, 728, 249 (1996).

    Article  CAS  Google Scholar 

  6. J. Jacques, A. Collet, and S. H. Wilen, Enantiomers, Racemates, and Resolution, Krieger Publ. Comp., Malabar (1994), p. 23.

    Google Scholar 

  7. R. G. Kostyanovsky, V. R. Kostyanovsky, G. K. Kadorkina, and K. A. Lyssenko, Mendeleev Commun., 13, 111 (2003).

    Article  Google Scholar 

  8. R. G. Kostyanovsky, Dokl. Akad. Nauk USSR, 139, 877 (1961).

    Google Scholar 

  9. R. P. Shibaeva and L. O. Atovmyan, Dokl. Akad. Nauk USSR , 160, 334 (1965).

    CAS  Google Scholar 

  10. V. I. Andrianov, R. G. Kostyanovsky, R. P. Shibaeva, and L. O. Atovmyan, Zh. Strukt. Khim., 8, 100 (1967).

    CAS  Google Scholar 

  11. K. D. Gundermann, G. Holtmann, H. J. Rose, and H. Schulze, Chem. Ber., 93, 1632 (1960).

    Article  Google Scholar 

  12. E. Kyburz, H. Els, S. Majnoni, G. Englert, C. Von Planta, A. Fürst, and P. A. Plattner, Helv. Chim. Acta, 49, 359 (1966).

    Article  CAS  Google Scholar 

  13. K. Nakajima, F. Takai, T. Tanaka, and K. Okawa, Bull. Chem. Soc. Jpn., 51, 1577 (1978).

    Article  CAS  Google Scholar 

  14. K. Jähnish, E. Schmitz, and E. Gründeman, J. Prakt. Chem., 321, 712 (1979).

    Article  Google Scholar 

  15. M. Turks, D. Zicāne, I. Rijkure, S. Beļakovs, in: Proceedings of 17th European Symposium on Organic Chemistry, Greece, Hersonissos, 10-15 July, 2011, p. 235.

  16. M. Turks, I. Rijkure, S. Beļakov, D. Zicāne, V. Kumpiņš, Ē. Bizdēna, A. Meikas, and A. Valkna, Khim. Geterotsikl. Soedin., 928 (2012). [Chem. Heterocycl. Compd., 48, 861 (2012)].

    Google Scholar 

  17. P. A. Levkin, V. Yu. Torbeev, D. A. Lenev, and R. G. Kostyanovsky, in: S. E. Denmark and J. S. Siegel (editors), Topics in Stereochemistry, Vol. 25, Wiley-Interscience, Hoboken (2006), p. 81.

  18. P. T. Trapentsier, I. Ya. Kalvins, E. E. Liepins, and E. J. Lukevics, Khim. Geterotsikl. Soedin., 350 (1983). [Chem. Heterocycl. Compd., 19, 283 (1986)].

    Google Scholar 

  19. A. F. Mishnev, M. F. Bundule, Ya. Ya. Bleidelis, P. T. Trapentsier, I. Ya. Kalvin’sh, and E. J. Lukevits, Khim. Geterotsikl. Soedin., 477 (1986). [Chem. Heterocycl. Compd., 22, 390 (1986)].

    Google Scholar 

  20. R. G. Kostyanovsky, V. P. Leshchinskaya, R. K. Alekperov, G. K. Kadorkina, L. L. Shustova, Yu. I. El’natanov, G. L. Gromova, A. E. Aliev, and I. I. Chervin, Izv. Akad. Nauk USSR, Ser. Khim., 2566 (1988).

  21. R. G. Kostyanovsky and O. A. Yuzhakova, Dokl. Akad. Nauk USSR, 159, 142 (1964).

    Google Scholar 

  22. R. G Kostyanovsky, Z. E. Samojlova, and I. I. Tchervin, Tetrahedron Lett., 9, 3025, (1968).

    Article  Google Scholar 

  23. J.-M. Lehn, in: Topics in Current Сhem., Vol. 15, Springer-Verlag, Berlin (1970), p. 311.

  24. W. B. Jennings, D. K. Boyd, in: J. B. Lambert and Y. Takeuchi (editors), Cyclic Organonitrogen Stereodynamics, VCH Publishers, N. Y. (1992), p. 105.

    Google Scholar 

  25. H. Oberhammer, Mendeleev Commun., 16, 136 (2006).

    Article  Google Scholar 

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Authors and Affiliations

  1. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow, 119991, Russia

    R. G. Kostyanovsky, G. K. Kadorkina, O. N. Krutius & I. I. Chervin

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  1. R. G. Kostyanovsky
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  2. G. K. Kadorkina
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  3. O. N. Krutius
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  4. I. I. Chervin
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Correspondence to R. G. Kostyanovsky.

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*Dedicated to Ivars Kalvinsh. For many years at the center of his interests was Leakadine – the subject of candidate’s (1976) and doctoral (1988) theses.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 936-941, June, 2012.

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Kostyanovsky, R.G., Kadorkina, G.K., Krutius, O.N. et al. 2-Carbamoylaziridine (Leakadine): diastereoselective transformations and stereoelectronic effect*. Chem Heterocycl Comp 48, 869–874 (2012). https://doi.org/10.1007/s10593-012-1068-1

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