Author (Your Name)

Sylvia Haller, Colby College

Date of Award


Document Type

Honors Thesis (Colby Access Only)


Colby College. Chemistry Dept.


Thomas W. Shattuck

Second Advisor

Bradford P. Mundy

Third Advisor

Charles Conover


Experimentally an unexpected reactivity difference was observed between a diester and imide system. Both A and C were thought to react similarly. However, while the diester, A, underwent a dienolate-mediated oxidation to form the corresponding alkene product, the imide, C, was unreactive.

This study examines this reactivity difference between the diester and the imide systems through a computational approach. The differences between the two systems will be considered at each step of the proposed mechanism. Also considered in this study is the appropriate method for handling dianions computationally.


Access note: full text is restricted to Colby College.


diesters, imides, dienolate-mediated oxidation, dianons

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