Circular Dichroism Studies of Ring-conf ormational and rotational Equilibria in 2-Isopropenylcyclohexanones
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The temperature-dependent circular dichroism of optically active β,γ-unsaturated ketones, (2<I>S</I>, 5<I>R</I>)-(−)-2-isopropenyl-2,5-dimethylcyclohexanone (<B>2</B>) and (2<I>S</I>, 5<I>R</I>)-(−)-2-isopropenyl-5-methylcyclohexanone (<B>3</B>), and of the corresponding saturated ketones, (2<I>S</I>, 5<I>R</I>)-(−)-2-isopropyl-2,5-dimethylcyclohexanone (<B>1</B>), has been measured at the n→π<SUP>*</SUP> transition in order to determine the relative disposition between the carbonyl group and the ethylenic bond of the isopropenyl group of the β,γ-unsaturated ketones. The compound (<B>2</B>) exhibited the sign of a Cotton effect opposite to that of the corresponding saturated compound (<B>1</B>), and the circular dichroism of the compound (<B>3</B>) behaved quite differently from menthone (<B>4</B>). The result has been discussed mainly in terms of the geometry of the carbonyl group and the ethylenic bond of the isopropenyl group. Thus, it has been concluded that the preferred conformations of the compounds (<B>1</B>), (<B>2</B>), and (<B>3</B>), are <B>1A</B>, <B>2A-III</B>, and <B>3A-I</B> respectively.
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