Type of Document Master's Thesis Author Davis, Edward A. URN etd-11142012-040248 Title Studies of sodium azide with tetraphenylcyclopentadienones and various analogs Degree Master of Science Department Chemistry Advisory Committee
Advisor Name Title Ogliaruso, Michael A. Committee Chair Hudlicky, Miles Committee Member McNair, Harold M. Committee Member Keywords
Date of Defense 1985-11-05 Availability restricted Abstract
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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