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8 . 6 Figure 3-6 Consider also the epimeric 2-methyl-trans-decalins (Figure 3-6). 8 observed) although the introduction of this substituent onto the parent does not change the number of anti-hydrogen interactions. 8 observed. 8 observed. 8 observed). 4 observed. 0. 41 Gauche y effects The situation becomes more complicated with the cis isomer of l,2-dimethylcyclohexane because of the presence of two equal energy (though mirror image) confonnations. Thus, the shift of each methyl group is the result of equal contributions from arrangements where the methyl is axial with three gauche interactions, and where it is equatorial, with only one gauche interaction.

L1 8 "( I-I I-Br l-CI 1-0H I-F 1-0Me l-CH20H l-COOMe l-CH20Ts l-COOH C2. 8 Substiw~t l-CH20H I-OMe l-COOMe I-F I-CH20Ts 1-0H l-COOH I-Br l-CI I-I C! lb~lily~nl ill. c2. c1. 8. 9 1 'Y C:i.. SubstilU~Dts C:i. :5. 5 () 'Y E3-Me E3-COOMe E3-0H A3-COOMe A3-NMe2 A3-Me A3-0H a. :3. 4 Mono- and Bicyc1ic Systems 35 References 1. W. , J. Phys. Chem. 74, 2680 (1970). 2. L. , Org. Magn. Reson. 13, 193 (1980). 3. Sadtler Standard Carbon-13 NMR Spectra, SadtIer Research Laboratories, Philadelphia, Pa 19104 (1976-1982).

3 'Y Anti interactions In the majority of situations, a substituent to a carbon that is 'Y but anti effects only a modest upfield shift. 5. 5), and thus there is a consistent trend from hydrogen to carbon to oxygen based upon the electronegativity of the substituent, presumably reflecting an increased, inductive withdrawal of electron density by the more electronegative substitutents. Notice, however, that the direction of the effect can not be explained by a direct, through bond interaction. It is likely that the effect is transmitted indirectly through the hydrogen on the carbon bearing the substituent.

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