Date of Award


Document Type


Degree Name

Master of Science (M.S.)



First Advisor

Donald K. Wedegaertner

First Committee Member

Charles A. Matuszak

Second Committee Member

Hershel Frye


A major purpose of this research was to investigate the mechanism of aryl azide addition to allenes. Much evidence has accumulated in support of a concerted mechanism for aryl azide additions to simple alkenes. Consistent with these findings, this addition is a symmetry allowed process. The analagous aryl azide additions to allenes have received little mechanistic study. The approach taken in this work was to probe the mechanism by using optically active 1,2-cyclonanadiene, observing the stereochemistry of the adduct formed upon addition of phenyl azide.

Another goal was to investigate the isomerization of the phenyl azide-1,2-cylononadiene adduct, 10-phenyl-10,11,12-triaza-△ 11 -bicyclo [7. 3. 0] duodec-1-ene (7) to the previously unknown aromatic isomer 4,5-heptamethylene-1-phenyl-1,2,3-triazole (14).



Included in

Chemistry Commons



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