Abstract
Using exo/endo and syn/anti to designate stereochemical relationships in bicyclo[3.1.1]heptanes creates problems because this system is based on the orientation of groups relative to the unique, smallest bridge. The M/G system defined in Chapter 6 for the bicyclo[2.2.2]octanes is equally applicable here. Briefly, a sense of rotation (clockwise or counterclockwise) is defined for an axis that passes through both bridgehead atoms based upon the ordering of assigned numbers for the atoms adjacent to atom 1. Substituents that are oriented with this sense of rotation are defined as M (mit) while those opposed are G (gegen). For monosubstituted compounds, the numbering system is defined so that the substituent is M.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References to Bicyclo[3.1.1]heptanes and related* systems
Andersen, N. H., Bissonette, P., Liu, C.-B., Shunk, B., Ohta, Y., Tseng, C.-L. W., Moore, A. and Huneck, S., Phytochem. 16, 1731 (1977).
Hall, M. C., Kinns, M. and Wells, E. J., Org. Magn. Reson. 21, 108 (1983).
Offermann, W., Org. Magn. Reson. 20, 203 (1982).
Forsyth, D. A., Mahmoud, S. and Giessen, B. C., Org. Magn. Reson. 19, 89 (1982).
Weigand, E. W. and Schneider, H.-J., Org. Magn. Reson. 12, 637 (1979).
Brun, P., Casanova, J., Hatem, J., Zahra, J. P. and Waegell, B., Org. Magn. Reson. 12, 537 (1979).
Szeimies, G., Schlosser, A., Philipp, F., Dietz, P. and Mickler, W., Chem. Ber. 111, 1922 (1978).
Bohlmann, F., Zeisberg, R. and Klein, E., Org. Magn. Reson. 7, 426 (1975).
Johnson, L. F. and Jankowski, W. C., “Carbon-13 NMR Spectra”, Wiley-Interscience, New York (1972).
Jautelat, M., Grutzner, J. B. and Roberts, J. D., Proc. Natl. Acad. Sci. 65, 288 (1970).
Holden, C. M. and Whittaker, D., Org. Magn. Reson. 7, 125 (1975).
Reisse, J., Piccinni-Leopardi, C., Zahra, J. P., Waegell, B. and Fournier, Org. Magn. Reson. 9, 512 (1977).
Lysenkov, V. I., Pekhk, T. I., Lippmaa, E. T. and Zheleznyak, T. L., J. Org. Chem. USSR 17, 1436 (1981).
Kane, B. J., Marcelin, G. and Traynor, S. G., J. Org. Chem. 45, 895 (1980).
Grover, S. H., Marr, D. H., Stothers, J. B. and Tan, C. T., Can. J. Chem. 53, 1351 (1975).
Della, E. W., Cotsaris, E., Hine, P. T. and Pigou, P. E., Aust. J. Chem. 34, 913 (1981).
Della, E. W. and Pigou, P. E., Aust. J. Chem. 36, 2261 (1983).
Della, E. W., Cotsaris, E. and Hine, P. T., J. Am. Chem. Soc. 103, 4131 (1981).
Della, E. W. and Pigou, P. E., J. Am. Chem. Soc. 104, 862 (1982).
Himmele, W. and Siegel, H., Tetrahedron Lett. 907 (1976).
Bessiere, Y., Grison, C. and Boussac, G., Tetrahedron 34, 1957 (1978).
Bessiere, Y., Barthélémy, M., Thomas, A. F., Pickenhagen, W. and Starkemann, C., Nouv. J. Chim. 2, 365 (1978).
Ericsson, A., Kowalewski, J., Liljefors, T. and Stilbs, P., J. Magn. Reson. 38, 9 (1980).
Thomas, A. F., Thommen, W. and Becker, J., Helv. Chim. Acta 64, 161 (1981).
Hoppmann, A., Weyerstahl, P. and Zummack, W., Liebigs Ann. Chem. 1547 (1977).
Marschall, H., Penninger, J. and Weyerstahl, P., Liebigs Ann. Chem. 49 (1982).
Gassman, P. G. and Proehl, G. S., J. Am. Chem. Soc. 102, 6862 (1980).
Gassman, P. G. and Oison, K. D., J. Am. Chem. Soc. 104, 3740 (1982).
Della, E. W. and Pigou, P. E., J. Am. Chem. Soc. 106, 1085 (1984).
Brown, H. C. and Ford, T. M., J. Org. Chem. 46, 647 (1981).
Burgar, M. I., Karba, D. and Kikelj, D., Farm. Vestnik 30, 253 (1979).
Formacek, V. and Kubeczka, K.-H., “Vorkommen und Analytik Ätherische Ole”, Kubeczka, K.-H. Ed., Thieme, Stuttgart, 1979, p 130.
Banert, K., Kirmse, W. and Wroblowsky, H.-J., Chem. Ber. 116, 3591 (1983).
Blunt, J. W. and Steel, P. J., Aust. J. Chem. 35, 2561 (1982).
Uchio, Y., Matsuo, A., Kakayama, M. and Hayashi, S., Tetrahedron Lett. 2963 (1976).
Sadtler Standard Carbon-13 NMR Spectra, Sadtler Research Laboratories, Inc., Philadelphia, Pa.
Rights and permissions
Copyright information
© 1987 Chapman and Hall Ltd
About this chapter
Cite this chapter
Whitesell, J.K., Minton, M.A. (1987). Bicyclo[3.1.1]heptanes. In: Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3161-9_9
Download citation
DOI: https://doi.org/10.1007/978-94-009-3161-9_9
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-7921-1
Online ISBN: 978-94-009-3161-9
eBook Packages: Springer Book Archive