Skip to main content
SpringerLink
Log in

The molecular and crystal structure of endo-2-methyl-7-hydroxy-7-oxo-N-phenyl-7-phosphabicyclo-[2.2.1] hept-2-ene-5,6-dicarboximide

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

Abstract

The structure of the title compound1 has been determined by X-ray crystallography analysis. The following crystal data were found: orthorhombic,Pca2l,a=9.60691),b=16.356(1),c=8.686(1) Å. Both the phospholane and phospholene rings involved in the 7-phosphabicyclo-[2.2.1] hept-2-ene system have almost regular envelope conformations, and the cyclohexene ring has a significantly deformed boat conformation. The low value of the C−P−C angle, 84.2(2)°, reflects the steric strain around the phosphorus bridge and may be responsible for the reactivity of esters and amides derived from1 in the O-insertion reaction with m-chloro-perbenzoic acid. The dihedral angle between the plane of the benzene and succinimide rings is 82.4(2)°.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Lee, J.B.; Uff, B.C.Q. Rew. 1967,21, 449.

    Google Scholar 

  2. Kashman, Y.; Awerbouch, O.Tetrahedron 1975,31, 45.

    Google Scholar 

  3. Quin, L.D.; Kisalus, J.C.; Mesch, K.A.J. Org. Chem. 1983,48, 4466.

    Google Scholar 

  4. Quin, L.D.; Marsi, B.G.J. Am. Chem. Soc. 1985,107, 3389.

    Google Scholar 

  5. Quin, L.D.; Szewczyk, J.; Szewczyk, K.M.; McPhail, A.T.J. Org. Chem. 1986,51, 3341.

    Google Scholar 

  6. Szewczyk, J.; Quin, L.D.; Yao, E.Y.Phosph. Sulf. Sil. 1990,54, 135.

    Google Scholar 

  7. Chiu, Y.H.; Lipscomb, W.N.J. Am. Chem. Soc. 1969,91, 4150.

    Google Scholar 

  8. Fitzgerald, A.; Campbell, J.A.; Smith, G.D.; Caughlan, C.N.J. Org. Chem. 1978,43, 3513.

    Google Scholar 

  9. Sheldrick, G.M.; Krüger, G.M.; Goddard, R.SHELXS-86. Crystallographic Computing 3; Oxford University Press, 1985.

  10. Walker, N.; Stuart, D.Acta Cryst. 1983,A39, 159.

    Google Scholar 

  11. Frenz, B.A. et al.SDP—Structure Determination Package; Enraf-Nonius: Delft, Holland, 1984.

    Google Scholar 

  12. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974.

  13. Duax, W.L.; Norton, D.A.Atlas of Steroid Structure; Plenum Press: New York, 1975.

    Google Scholar 

  14. Bukowska-Strzyżewska, M.; Dobrowolska, W.; Glowiak, T.Acta Cryst. 1980,B36, 3167.

    Google Scholar 

  15. Bukowska-Strzyżewska, M.; Dobrowolska, W.; Głowiak, T.Acta Cryst. 1980,B36, 2476.

    Google Scholar 

  16. Dobrowolska, W.; Bukowska-Strzyżewska, M.Acta Cryst. 1980,B36, 890.

    Google Scholar 

  17. Taira, Z.; Takayama, Ch.; Terada, H.J. Chem. Soc. Perkin Trans. 1988,II, 1440.

    Google Scholar 

  18. Cambridge Structural Database; 1991.

Download references

Author information

Authors and Affiliations

  1. Institute of Technical Biochemistry, Technical University of Łódź, Stefanowskiego 4/10, 90-924, Łódź, Poland

    M. W. Wieczorek & G. D. Bujacz

  2. Institute of Organic Chemistry, Technical University of Łódź, Zwirki 36, 90-924, Łódź, Poland

    R. Bodalski

  3. Department of Chemistry, University of Massachusetts, 01003, Amherst, Massachusetts

    Louis D. Quin

Authors
  1. M. W. Wieczorek
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. D. Bujacz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. Bodalski
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Louis D. Quin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wieczorek, M.W., Bujacz, G.D., Bodalski, R. et al. The molecular and crystal structure of endo-2-methyl-7-hydroxy-7-oxo-N-phenyl-7-phosphabicyclo-[2.2.1] hept-2-ene-5,6-dicarboximide. J Chem Crystallogr 24, 431–435 (1994). https://doi.org/10.1007/BF01666090

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01666090

Key Words

Search

Navigation