The reaction of sodium azide with 2-p-chloro- and 2-p—methoxyphenyl—
3,4,5-triphenyl—2,4-cyclopentadien—I—one was studied to determine if the
substituent would have any appreciable effect on the product distribution
of the corresponding l,5,7,8—tetraphenyl-2,3,4—triazabicyclo[3.3.0]octa-2,7-dien-6-ones and the 3,4,5,6—tetraphenyl—2(lH)—pyridinones that were
formed by an acid catalyzed rearrangement. It was found that the chloro
substituent had no effect on the reaction. The methoxy substituent had
a moderate effect in that the product arising from the stabilized intermediate
cation was favored by a ratio of approximately 3 to l.
The two simple linear analogs studied were l,2,3,3—tetraphenyl-2-
propen-l-one and 3,4,4-triphenyl-3—buten—2—one. These compounds did not
react with azide, presumably due to charge delocalization. Also
studied as a cyclic analog was 2,7-diphenyltropone which did not react
due to the aromatic character of the tropone ring system. A reaction did
occur with diphenylcyclopropenone to give an unidentified product.
However, the reaction did not take place in the same fashion as for the
tetracyclones.
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