Abstract
The structure of a compound derived from a symmetrical cage diketone in which one of the ketone C=O groups has been converted into a ketal is reported. An investigation into reasons for the selective functionalization resulted in the isolation of acis, cisoid, cis linear triquinane derivative in which both ketones are converted to ketals that share a transannular oxygen atom. Crystal data:2, monoclinic,P21/c,a=7.6298(9),b=7.673(3),c=22.125(3)Å,β=97.59(1)°,V=1283.9(5)Å3, andR=0.048 (1001 reflections);4, triclinic,P¯1,a=7.3864(9),b=9.6362(9),c=10.3889(9)Å,α=75.749(6),β=76.300(8), γ=83.100(8)°,V=694.8(4)Å3, andR=0.088 (1284 reflections).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G., and Taylor, R. (1987)J. Chem. Soc., Perkin Trans. II, S1.
Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Polidori, G., Spagna, R., and Viterbo, D. (1989)J. Appl. Cryst. 22, 389–393.
Cookson, R. C., Cnindwell, E., Hill, R. R., and Hudec, J. (1964)J. Chem. Soc., 3062.
Coxon, J. M., Fong, S. T., Steel, P. J., Bott, S. G., Marchand, A. P., and Zope, U. R. (1993)Acta Crystallogr., Sect. C;Cryst. Struct. Commun., in press.
Eaton, P. E., Cassar, L., Hudson, R. A., and Hwang, D. R. (1976)J. Org. Chem. 41, 1445.
Enraf-Nonius (1990)MolEN, an interactive structure solution procedure. (Enraf-Nonius, Delft, The Netherlands).
Johnson, C. K. (1976)ORTEP II. Report ORNL-5138. (Oak Ridge National Laboratory, Tenn.).
Main, P., Fiske, S. J., Hull, S. E., Lessinger, L., Germain, G., DeClerq, J. P., and Woolfson, M. M. (1980)MULTAN80. A system of computer programs for the automatic solution of crystal structures from x-ray diffraction data. (Univ. of York, England).
Marchand, A. P. (1989)Advances in theoretically interesting molecules, Vol. 1. R. P. Thummel, ed. (JAI Press, Greenwich, CT, pp. 357–399).
Marchand, A. P. (1991)SYNETT 73–79.
Marchand, A. P., and Allen, R. W. (1974)J. Org. Chem. 39, 1596.
Mason, M. R., Smith, J. M., Bott, S. G., and Barron, A. R. (1993)J. Am. Chem. Soc. 115, 4971.
Mehta, G., Srikrishna, A., Reddy, A. V., and Nair, M. S. (1981)Tetrahedron 37, 4543.
Osawa, E., and Kanematsu, K. (1986)Molecular structure and energetics, Vol. 3. J. F. Liebman and A. Greenberg (eds.) (VCH Publishers, Deerfield Beach, FL, pp. 329–369).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bott, S.G., Raja Gopal, D., Durga Prasad, A. et al. Structures of two ketals derived from a pentacyclic cage diketone. Journal of Crystallographic and Spectroscopic Research 23, 1013–1017 (1993). https://doi.org/10.1007/BF01185553
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01185553