13C NMR Studies of some Bicyclo[2.2.2]Octanones.a Characterization of the Isomeric 1,5,5,8-Tetramethylbicyclo[2.2.2]Octan-2-Ones

  • K. R. Stephens
  • J. B. Stothers
  • C. T. Tan
Part of the Environmental Science Research book series (ESRH, volume 4)


The 13C nmr spectra of a series of sixteen bicyclo[2.2.2]octenones and octanones have been determined to examine the variation of 13C shieldings with methyl substitution. The well-defined effects arising from 1,4-nonbonded interactions are apparent and are useful for stereochemical assignments. Evidence is presented to show that closely neighboring ´ carbons experience deshielding effects, in sharp contrast to the influence of steric crowding on y carbons. The 13C shieldings observed for 1,5,8,8-tetramethylbicyclo[2.2.2]oct-5-en-2-one and the isomeric saturated bicyclooctanones obtained therefrom establish their structures.


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Copyright information

© Springer Science+Business Media New York 1974

Authors and Affiliations

  • K. R. Stephens
    • 1
  • J. B. Stothers
    • 1
  • C. T. Tan
    • 1
  1. 1.Department of ChemistryUniversity of Western OntarioLondonCanada

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