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.
Similar content being viewed by others
REFERENCES
Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: NY, 1989.
Snatzke, G.; Zanati, G. Liebigs Ann. Chem. 1965,684, 62.
Nerdel, F.; Janowsky, K.; Frank, D. Tetrahedron Lett. 1965, p. 2979.
Altman, J.; Babad, E.; Itzchaki, J.; Ginsburg, D. Tetrahedron 1966, (Suppl. 8), p. 279.
(a) Thompson, H. W. Tetrahedron Lett. 1966, p. 6489; (b) Thompson, H. W. J. Org. Chem. 1968, 33, 621.
Fieser, L. F.; Dunn, J. T. J. Amer. Chem. Soc. 1936,58, 1054.
Diels, O.; Friedrichsen, W. Liebigs Ann. Chem. 1934,513, 145.
Fieser, L. F.; Hershberg, E. B. J. Amer. Chem. Soc. 1936,58, 2314.
Alder, K.; Backendorf, K. H. Chem. Ber. 1938,71, 2199.
Thompson, H. W. J. Org. Chem. 1967,32, 1222.
Zewge, D.; Thompson, H. W.; Brunskill, A. P. J.; Lalancette, R. A. Acta Crystallogr. 1999,C55, 1370.
Giovanni, E.; Wegmüller, H. Helv. Chim. Acta 1958,41, 933.
Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981,46, 3936.
XSCANS Single-Crystal X-ray Analysis Software, Version 2.2, 1996. Siemens Analytical X-ray Instruments Inc., Madison, WI.
Sheldrick, G. M. SHELXTL Structure-Determination Program, Version 5.10, 1997. Bruker AXS Inc., Madison, WI.
Pasteur, L. Ann. Chim. Phys. 1848,24, 442.
Chen, C.-D.; Brunskill, A. P. J.; Hall, S. S.; Lalancette, R. A.; Thompson. H. W. Acta Crystallogr. 2000,C56, 1148.
Steiner, T. Chem. Commun. 1997, p. 727.
Steiner, T.; Desiraju, G. R. Chem. Commun. 1998, p. 891.
Author information
Authors and Affiliations
Rights 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
Issue Date:
DOI: https://doi.org/10.1023/A:1020513504492