Abstract
The syntheses and crystal structures of pentacyclo[9.4.1.05,14.07,13.012,15]hexadecane-3,9-dione (2), a novel C16 diketone with potential inclusion ability, and the products of the reaction of2 withn-butyllithium andmeso-erythritol (i.e.,meso-1,2,3,4-butanetetrol) are described. Crystal data:2·H2O, orthorhombic,Pmmn,a=10.7385(8),b=9.0188(6),c=6.8411(4)Å,V=662.55(7)Å3, andR=0.039 (379 reflections);3 (product from reaction withn-butyllithium), triclinic,P¯1,a=8.7192(7),b=10.9351(8),c=12.1842(8)Å,α=68.933(5),β=75.850(6), γ=80.309(6)°,V=1047.0(1)Å3, andR=0.081 (1811 reflections);4 (product from reaction with erythritol), triclinic,P¯1,a=7.7224(8),b=10.1976(8),c=10.7021(9)Å,α=85.405(7),β=85.766(8), γ=76.056(7)°,V=814.0(1)Å3, andR=0.052 (1471 reflections).
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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.
Enraf-Nonius (1990)MolEN, an interactive structure solution procedure. (Enraf-Nonius, Delft, The Netherlands).
Johnson, C. K. (1976)ORTEPII. 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)SYNLETT, 73–79.
Mason, M. R., Smith, J. M., Bott, S. G., and Barron, A. R. (1993)J. Am. Chem. Soc. 115, 4971–4984.
Mehta, G. and Padma, S. (1991)Tetrahedron 47, 7807–7820.
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Bott, S.G., Marchand, A.P. & Raja Gopal, D. Synthesis and characterization of a novel pentacyclic C16 diketone and derivatives. Journal of Crystallographic and Spectroscopic Research 23, 849–855 (1993). https://doi.org/10.1007/BF01195731
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DOI: https://doi.org/10.1007/BF01195731