Abstract
The relationship between Zimmermann reaction and base-catalyzed deuterium exchange reactivity of 16- and 17-oxosteroids together with some simple ketones has been investigated. With regard to the simple ketones such as cyclopentanone (I), cyclohexanone (II) and diethyl ketone (III) the sequential order of the deuterium exchange activity was found to be in qualitative agreement with that of the rate of Zimmermann reaction as follows : I>II≈III. The Zimmermann complex derived from cholestan-3-one, mp178-180°, was isolated and assigned to the structure of 2α-(2, 4-dinitrophenyl) cholestan-3-one on the basis of the nuclear magnetic resonance spectrum. The spectroscopic properties of Zimmermann complexes produced from the cyclic ketones are also described.
