Skip to main content
Log in

2,6-Dioxa-3,7-dioxotricyclo[3.3.3.01,5]undecane, a Propellanoid Dilactone Representing a New Tricyclic Ring System

  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The title material, tetrahydro-3a,6a-propanofuro-[3,2-b]furan-2,5-dione (C9H10O4), is a new compound representing a previously unreported ring system. Its asymmetric unit lacks an axis of symmetry because of nonplanarity in the carbon ring. Although the bulk material is racemic, only single enantiomers are incorporated into the crystal, which is unusually dense. Several intermolecular C–H⋅ ⋅ ⋅O close contacts were found.

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. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: NY, 1989.

    Google Scholar 

  2. Snatzke, G.; Zanati, G. Liebigs Ann. Chem. 1965,684, 62.

    Google Scholar 

  3. Nerdel, F.; Janowsky, K.; Frank, D. Tetrahedron Lett. 1965, p. 2979.

  4. Altman, J.; Babad, E.; Itzchaki, J.; Ginsburg, D. Tetrahedron 1966, (Suppl. 8), p. 279.

  5. (a) Thompson, H. W. Tetrahedron Lett. 1966, p. 6489; (b) Thompson, H. W. J. Org. Chem. 1968, 33, 621.

  6. Fieser, L. F.; Dunn, J. T. J. Amer. Chem. Soc. 1936,58, 1054.

    Google Scholar 

  7. Diels, O.; Friedrichsen, W. Liebigs Ann. Chem. 1934,513, 145.

    Google Scholar 

  8. Fieser, L. F.; Hershberg, E. B. J. Amer. Chem. Soc. 1936,58, 2314.

    Google Scholar 

  9. Alder, K.; Backendorf, K. H. Chem. Ber. 1938,71, 2199.

    Google Scholar 

  10. Thompson, H. W. J. Org. Chem. 1967,32, 1222.

    Google Scholar 

  11. Zewge, D.; Thompson, H. W.; Brunskill, A. P. J.; Lalancette, R. A. Acta Crystallogr. 1999,C55, 1370.

    Google Scholar 

  12. Giovanni, E.; Wegmüller, H. Helv. Chim. Acta 1958,41, 933.

    Google Scholar 

  13. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981,46, 3936.

    Google Scholar 

  14. XSCANS Single-Crystal X-ray Analysis Software, Version 2.2, 1996. Siemens Analytical X-ray Instruments Inc., Madison, WI.

  15. Sheldrick, G. M. SHELXTL Structure-Determination Program, Version 5.10, 1997. Bruker AXS Inc., Madison, WI.

    Google Scholar 

  16. Pasteur, L. Ann. Chim. Phys. 1848,24, 442.

    Google Scholar 

  17. Chen, C.-D.; Brunskill, A. P. J.; Hall, S. S.; Lalancette, R. A.; Thompson. H. W. Acta Crystallogr. 2000,C56, 1148.

    Google Scholar 

  18. Steiner, T. Chem. Commun. 1997, p. 727.

  19. Steiner, T.; Desiraju, G. R. Chem. Commun. 1998, p. 891.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tsao, J.F., Thompson, H.W. & Lalancette, R.A. 2,6-Dioxa-3,7-dioxotricyclo[3.3.3.01,5]undecane, a Propellanoid Dilactone Representing a New Tricyclic Ring System. Structural Chemistry 13, 455–458 (2002). https://doi.org/10.1023/A:1020513504492

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1020513504492

Navigation