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The intensity of 1,3-allylic strain is illustrated by the finding that cis-2,6-dimethylcyclohexanone oxime adopts the conformation with the methyls axial, see
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The intensity of 1,3-allylic strain is illustrated by the finding that cis-2,6-dimethylcyclohexanone oxime adopts the conformation with the methyls axial, see: Durand, R.; Geneste, P.; Moreau, C.; Pavia, A. A. Org. Magn. Reson. 1974, 6, 73.
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Other, sometimes spectacular examples of the effects of allylic strain on conformation preferences include
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This also has been observed in the reduction of iminium salts of 17-keto steroids containing an adjacent methyl with LiAlH4. The cis isomers were the only reported products
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This also has been observed in the reduction of iminium salts of 17-keto steroids containing an adjacent methyl with LiAlH4. The cis isomers were the only reported products: Scribner, R. M. J. Org. Chem. 1965, 30, 3203.
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