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Date of Award


Document Type


Degree Name

Doctor of Philosophy (Ph.D.)


Graduate School

First Advisor

Donald K. Wedegaertner

First Committee Member

Charles Matuszak

Second Committee Member

Paul H. Gross

Third Committee Member

Madhukar Chaubal


The strained cyclic allene intermediates of 1,2-cyclohexadiene, 1,2-cycloheptadiene and 1,2-cyclooctadiene have been successfully generated by the debromination of their corresponding 2,3-dibromocycloalkenes. Evidence for their intermediate existence was obtained by trapping them with the Diels-Alder trapping agent 2,5-diphenyl 1-3,4-benzofuran and by isolating the corresponding addition products.

The goal of this study was to generate the transitory cyclic allenes 1,2-cyclooctadiene, 1,2-cycloheptadiene and 1,2-cyclohexadiene and to investigate some aspects of their chemistry. Evidence for the intermediate existence of these strained cyclic allenes has been found by generating them by the debromination of their corresponding 2,3-dibromocycloalkenes and by trapping the generated cycloallene intermediates with the Diels-Alder trapping agent 2,5-diphenyl-3,4-benzofuran.

In order to carry out this study, it became necessary to synthesize 2,3-dibromocyclooctene and 2,3-dibromocycloheptene. 2,3-Dibromocyclohexene had been previously prepared. The synthetic sequence employed to obtain these compounds is summarized by Equations 2 and 3.





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