Document Type


Date of Award


Degree Name

Master of Science in Chemistry - (M.S.)


Chemical Engineering, Chemistry and Environmental Science

First Advisor

Arthur Greenberg

Second Advisor

Carol A. Venanzi

Third Advisor

Barbara B. Kebbekus


While 1-Azabicyclo(3,3,1)nonan-2-one was originally thought to be difficult to synthesize, two different methods (DCC and di-n-butyltin oxide) will produce it with high yield. DCC is a strong reagent for absorbing water; the di-n-butyltin oxide method uses a Dean-Stark to remove water and is very useful. Bredt's rule influences the synthesis and stability of the N-bridgehead bicyclic lactams, this is apparent in the lactam series in the behavior of the (2,2,2) compounds and the (3,2,1) compound which we tried unsuccessfully to synthesize.

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