Abstract
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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Stephens, K.R., Stothers, J.B., Tan, C.T. (1974). 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. In: Haque, R., Biros, F.J. (eds) Mass Spectrometry and NMR Spectroscopy in Pesticide Chemistry. Environmental Science Research, vol 4. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4526-8_14
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