Skip to main content
Log in

Synthesis and crystal structure of (+)-(2R,3R)-N, N′-bis-trityl-2,3-bis-aziridine

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

A new C2 symmetric bis-aziridine derivative was synthesized starting from L-(+)-tartaric acid. The molecular structure of (+)-(2R, 3R)-N, N′-bis-trityl-2,3-bis-aziridine 4, was determined by 1H, 13C NMR and elemental analysis and was confirmed by single-crystal X-ray diffraction. Crystal data for 4: C42H36N2, orthorhombic, space group: P212121, a = 12.7633(14), b = 14.5661(6), c = 17.4184(14) Å, and Z = 4.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Tanner, D. Angew. Chem. 1994, 106, 625, and references cited therein; (b) Osborn, H.M.I.; Sweeney, J. Tetrahedron Asymmetry 1997, 8, 1693, and references cited therein.

    Google Scholar 

  2. Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 4211; (b) Tanner, D. Tetrahedron 1992, 48, 6079.

    Google Scholar 

  3. Brimacombe, J.S.; Hanna, R.; Tucker, C.N. J. Chem Soc Perkin Trans. 1 1983, 2277; (b) Gurjar, M.K.; Patil, V.J.; Yadav, J.S.; Rama Rao, A.V. Carbohydr. Res. 1984, 129, 267.

    Google Scholar 

  4. Sommerdijk, N.A.J.M.; Buijnsters, P.J.J.A.; Akdemir, H.; Geurts, D.G.; Nolte, R.J.M.; Zwanenburg, B. J. Org. Chem. 1997, 62, 4955.

    Google Scholar 

  5. Deyrup, J.A. In Small Ring Heterocycles, Part 1, Hassner, A., Ed.; Wiley Interscience: New York, 1983; (b) Bartok, M.; Lang, K.L. In Small Ring Heterocycles, Part 3, Hassner, A., Ed.; Wiley Interscience: NewYork, 1985; (c) Legters, J.: Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays Bas. 1992, 111, 1; (d) Tanner, D. Pure Appl. Chem. 1993, 65, 1319.

    Google Scholar 

  6. Pfannemüller, B.; Welte, W. Chem. Phys. Lipids 1985, 37, 227; (b) Nakashima, N.; Asakuma, S.; Kunitake, T. J. Am. Chem. Soc. 1985, 107, 509; (c) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414; (d) Hafkamp, R.J.H.; Feiters, M.C.; Nolte, R.J.M. Angew Chem. Int. Ed. Engl. 1994, 33, 986; (e) Sommerdijk, N.A.J.M.; Buijnsters, P.J.J.A.; Akdemir, H.; Geurts, D.G.; Pistorius, A.M.A.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. Chem. Eur. J. 1998, 4, 127.

    Google Scholar 

  7. Menger, F.M.; Littau, C.A. J. Am. Chem. Soc. 1991, 113, 1451; (b) Menger, F.M.; Littau, C.A. J. Am. Chem. Soc. 1993, 115, 10083; (c) Klotz, F.; Cuccia, L.A.; Mohammed, N.; Just, G.; Lennox, R.B. J. Chem. Soc. Chem. Commun. 1994, 2043; (d) Sommerdijk, N.A.J.M.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. Recl. Trav. Chim. Pays Bas 1994, 113, 194; (e) Sommerdijk, N.A.J.M.; Hoeks, T.H.L.; Synak, M.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. J. Am. Chem. Soc. 1997, 119, 4338; (f) Sommerdijk, N.A.J.M.; Lambermon, H.H.L.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. Chem. Commun. 1997, 1423; (g) Jennings, K.; Marshall, I.; Birrell, H.; Edwards, A.; Haskins, N.; Sodermann, O.; Kirby, A.J.; Camilleri, P. J. Chem. Soc. Chem. Commun. 1998, 1951.

    Google Scholar 

  8. Gelder, R. de; Graaff, R.A.G. de; Schenk, H. Acta Crystallogr. 1993, A49, 287.

    Google Scholar 

  9. Sheldrick, G.M. SHELXL-93. Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1993.

    Google Scholar 

  10. Spek, A.L. Acta Crystallogr. 1990, A46, C-34.

    Google Scholar 

  11. Carmack, M.: Kelly, C.J. J. Org. Chem. 1968, 33, 2171; (b) Seebach, D.; Hungerbühler, E. In Modern Synthetic Methods vol. 2, Sheffold, R., Ed., Otto Salle Verlag: Frankf./M, 1980; p 155; (c) Rubin, L.J.; Lardy, H.A.; Fischer, H.O.L. J. Am. Chem. Soc. 1952, 74, 425.

    Google Scholar 

  12. Golobov, Y.G.; Zhmurova, I.N.; Kasukhin, L.F. Tetrahedron 1981, 37, 437; (b) Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 4211; (c) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881.

    Google Scholar 

  13. North, A.C.T.; Philips, D.C.: Mathews, F.S. Acta Crystallogr. 1968, A24, 351.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buijnsters, P.J.J.A., van der Reijden, F.P., Feiters, M.C. et al. Synthesis and crystal structure of (+)-(2R,3R)-N, N′-bis-trityl-2,3-bis-aziridine. Journal of Chemical Crystallography 29, 179–183 (1999). https://doi.org/10.1023/A:1009518010352

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1009518010352

Navigation