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Reaction of tetrahydropyranyl azides with 5-R-bicyclo[2.2.1]-2-heptenes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 5-R-bicyclo[2.2.1]-2-heptenes with 3-azido-4-hydroxy-4-methyltetrahydropyran and 4-azidomethyl-4-hydroxytetrahydropyran, obtained by opening the oxirane ring in epoxytetrahydropyrans with sodium azide, leads to the formation of N-tetrahydropyranylaziridines with 100% stereoselectivity.

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References

  1. V. B. Mochalin, Z. I. Smolina, A. G. Vul'fson, and B. V. Unkovskii, Zh. Obshch. Khim.,44, 2334 (1974).

    Google Scholar 

  2. U. G. Ibatullin, D. Ya. Mukhametova, S. A. Vasil'eva, R. F. Talipov, L. V. Syurina, M. G. Safarov, and S. R. Rafikov, Izv. Akad. Nauk. Ser. Khim., No. 9, 2114 (1982).

    Google Scholar 

  3. S. A. Vasil'ev, T. Sh. Mukhametyanova, and M. G. Safarov, Zh. Org. Khim.,27, No. 4, 778 (1991).

    Google Scholar 

  4. U. G. Ibatullin, L. V. Syurina, S. A. Vasil'eva, T. B. Semenova, and M. G. Safarov, Khim. Geterotsikl. Soedin., No. 11, 1455 (1984).

    Google Scholar 

  5. U. G. Ibatullin, S. A. Vasil'ev, Z. Kh. Karimova, I. Z. Latypova, and M. G. Safarov, Khim. Geterotsikl. Soedin., No. 12, 1604 (1989).

    Google Scholar 

  6. O. M. Nefedov, Chemistry of Carbenes and Small Sized Cyclic Compounds, Mir, Moscow (1989), p. 71.

    Google Scholar 

  7. R. V. Schleyer, J. Am. Chem. Soc.,89, 701 (1967).

    Article  Google Scholar 

  8. L. H. Zalkov and A. C. Oehlschlager, J. Org. Chem.,28, 3303 (1963).

    Google Scholar 

  9. K. Tore, K. Kitahonoki, and Y. Tanako, J. Am. Chem. Soc.,85, 908 (1963).

    Google Scholar 

  10. P. Laszlo and P. Schleyer, J. Am. Chem. Soc.,86, 1171 (1964).

    Article  Google Scholar 

Download references

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Bashkir State University, Ufa 450074. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 893–897, July, 1997.

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Vasil'eva, S.A., Abzalov, A.Z. & Safarov, M.G. Reaction of tetrahydropyranyl azides with 5-R-bicyclo[2.2.1]-2-heptenes. Chem Heterocycl Compd 33, 778–782 (1997). https://doi.org/10.1007/BF02253025

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  • DOI: https://doi.org/10.1007/BF02253025

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