The reaction of sodium azide with 2-p-chloro- and 2-p–methoxyphenyl–3,4,5-triphenyl–2,4-cyclopentadien– Iâ 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)â 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–2â 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. / Master of Science

The acld-oata17zed oyclodehydrat1on reaction of 2-benzylphenyl l-naphthyl ketone gives two products! 9-(1-naphthyl)anthracene, the expected product and in addition lO-phenyl-l,2-benzanthracene. This second product is the one expected it the ketone were subjected to the conditions of an .Elba reaction. The effect of substituents on the course of this reaction was investigated by synthesizing six 2-benzylphenyl 1- and 2-naphthyl ketones and subjecting each of them to the acid catalyzed reaction and to Elba reaction conditions. Of the six ketones, two had unsubstituted benzyl groups, two had 3'-methyl groups in the benzyl group and the remaining two had ,'-tr1fluoromethyl groups. The original finding was confirmed and the other ketones that cyoilzed by either treatment gave the expected products. When 2-(3'-methylbenzyl) 2-naphthl1 ketone was subjected to Elbs reaction conditions, 9-(2-naphthyl)anthraoene, the product of aromatic oyclodehydrat1on, was obtained. An explanation oft the unusual experimental results is suggested. The results of treat1ng the ketones w1th alumina and w1th l1qu1d hydrogen fluoride are reported. / Ph. D.