Carbon-13 NMR studies of 9-methyl-9-azabicyclo [3.3. 1] nonane and related compounds

SF Nelsen, GR Weisman, EL Clennan…

Index: Nelsen,S.F. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 6893 - 6896

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Citation Number: 18

Abstract

Abstract: The I3C NMR spectra for 9-methyl-9-azabicyclo [3.3. 1] nonane (1) and 2-methyl-2- azaadamantane (2) were studied at low temperature. Comparison with the related hydrocarbons (N replaced by CH) reveals that the p carbons anti to the nitrogen lone pair are shifted upfield 1-2 ppm more than the syn carbons. Inversion barriers for 1 and 2 were determined by line shape analysis to be about 8.1 kcal/mol at-90" C. 9-Dimethylamino-9- ...