1980 Volume 53 Issue 8 Pages 2304-2308
The syn-anti isomerization of acetylbenzocrown ether oximes was stimulated by the complex-formation with sodium ion. The photolysis of these oximes gave mother ketones and amides through an oxaziridine intermediate. The photolysis of the oximes was depressed by the formation of host-guest complexes. Reactivity in the photolysis of the crown ether oximes corresponds to that of 3,4-dimethoxyacetophenone oxime, whereas the reactivity of the complexed crown ether oxime with sodium ion corresponds to that of p-cyanoacetophenone oxime. Such behavior is explained by the change of the electronic properties of excited states of acetophenone oxime chromophore, which enhances the intersystem crossing.
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