Abstract
The pinacol resulting from sodium promoted reductive coupling of pentacyclo[5.4.0.02,6.-03,10.05,9]undecane-8,11-dione monoethylene ketal possesses a conformation, dictated by intramolecular hydrogen bonding, that lies midway between eclipsed and staggered. The C−C and C−O distances in the pinacol unit are, respectively, longer and shorter than usual, and all parameters are as expected.
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References
Marchand, A. P. InAdvances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT; 1989; Vol. 1, pp 357–399;
Marchand, A. P.Synlett 1991,73.
Marchand, A. P.; Liu, Z.; Gadgil, V. R.; Burritt, A.; Bott, S. G.Tetrahedron Lett., submitted for publication, 1995.
Eaton, P. E.; Cassar, L.; Hudson, R. A.; Hwang, D. R.J. Org. Chem. 1976,41, 1445.
Mason, M. R.; Smith, J. M.; Bott, S. G.; Barron, A. R.J. Am. Chem. Soc. 1993,115, 4971.
Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Polidori, G.; Spagna, R.; Viterbo, D.J. Appl. Cryst. 1989,22, 389.
Enraf-Nonius.MolEN, An Interactive Structure Solution Procedure; Enraf-Nonius: Delft, The Netherlands. 1990.
International Tables for X-ray Crystallography. Vol. IV; Kynoch Press: Birmingham, UK, 1974; pp 99, 149.
Johnson, C. K.ORTEPII Report ORNL-5138, 1976; Oak Ridge National Laboratory, Tennessee.
For a representative sample of pinacol structures, see: (a) Wei, K-T.; Ward, D. L.Acta. Crystallogr. Sect. B,1978, B34, 2010;
Stora, C.; Jeannin, Y.; Dana, G.; Touboul, E.Acta. Crystallogr. Sect. B,1979, B35, 420
Duesler, E. N.; Mondragon, M.; Tapscott, R. E.Acta. Crystallogr. Sect. C,1984, C40, 1286
Bourne, S. A.; Nassimbeni, L. R.; Toda, F.J. Chem. Soc., Perkin Trans. 2 1991, 1335, and references therein.
Allen, F. H.; Kennard O.; Watson, D. G.; Brammer, L.; Orpen A. G.; Taylor, R.J. Chem. Soc., Perkin Trans. II1987, S1.
Ösawa, E.; Kanematsu, K.Molecular Structure and Energetics. Vol. 3; Liebman, J. F.; Greenberg, A. Eds.: VCH: New York, 1986; pp 329–369
Marchand, A. P.; Huang, C.; Kaya, R.; Baker, A. D.; Jemmis, E. D.; Dixon, D. A.J. Am. Chem. Soc. 1987,107, 7095.
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Bott, S.G., Marchand, A.P. & Rajagopal, D. Structure of a PCU-derived pinacol formed via sodiumpromoted reductive dimerization of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione monoethylene ketal. J Chem Crystallogr 25, 517–520 (1995). https://doi.org/10.1007/BF01665710
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DOI: https://doi.org/10.1007/BF01665710