Title page for ETD etd-11142012-040248

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
  • Ketones
Date of Defense 1985-11-05
Availability restricted

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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