Abstract
Crystal structure determination reveals that the unknown cycloaddition product between maleic anhydride, cyclopentadiene, and 1,2-bis(dibromomethyl)benzene has a nona-cyclic centrosymmetric structure. The compound was studied as DMF solvate (1∶2). There is no significant intermolecular interaction between the title molecule and the DMF. Packing is in layers for both molecular species. A possible mechanism of formation of the title compound is discussed.
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Cava, M. P., Deana, A. A., and Muth, K. (1959)J. Am. Chem. Soc. 81, 6458.
Charlton, J. L., and Alauddin, M. M. (1987)Tetrahedron 43, 2873.
Desiraju, G. R. (1991)Acc. Chem. Res. 24, 290.
Destro, R., Filippini, G., Gramaccioli, C. M., and Simonetta, M. (1969)Acta Crystallogr. B 25, 2465.
Diels, O., and Alder, K. (1928)Liebigs Ann. Chem. 460, 98.
Hundt, R. (1979)KPLOT Program for plotting and investigating crystal structures (Universität Bonn, Germany).
Johnson, C. K. (1970)ORTEP Program for plotting crystal structures on a plotter (Oak Ridge National Laboratories, TN).
Kerdesky, F. A. J., Ardecky, R. J., Lakshmikantham, M. V., and Cava, M. P. (1981)J. Am. Chem. Soc. 103, 1992.
Kohnke, F. H., and Stoddart, J. F. (1992a)Pure Appl. Chem., in press.
Kohnke, F. H., Mathias, J. P., and Stoddart, J. F. (1992b)Top. Curr. Chem., in press.
Sheldrick, G. M. (1986)SHELX-86 Program for crystal structure solution (Universität Göttingen, Germany).
Sheldrick, G. M. (1976)SHELX-76 Program for crystal structure determination (University of Cambridge, England).
Stoddart, J. F. (1988)Chem. Br. 24, 1203.
Watson, W. H. (ed.) (1983)Stereochemistry and reactivity of systems containing π-electrons (Verlag Chemie, Deerfield Beach, Florida).
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Reutel, C., Weber, E., Henseler, U. et al. Crystal and molecular structure of the cycloaddition product between maleic anhydride, cyclopentadiene, and 1,2-bis(dibromomethyl)benzene as DMF solvate (1∶2). Journal of Crystallographic and Spectroscopic Research 23, 55–60 (1993). https://doi.org/10.1007/BF01161288
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DOI: https://doi.org/10.1007/BF01161288