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Synthetic Approach To Hexaoxa[6]Peristylanes. A Novel Ddq-Induced Oxidative Rearrangement, Douglas Arthur Otte

Honors Theses

The structural beauty and interesting bonding properties of polycyclic cage compounds have been a source of fascination to many chemists. In this work, progress toward the synthesis of large oxabowl systems, such as hexaoxa[6]peristylane and its derivative dipbenylhexaoxa[6)peristylane, is described. Thus, the adduct obtained from the cycloaddition of maleic anhydride and cyc!ooctatetraene is converted into key dicarbonyl intermediates. Subsequently, the ozonolysis of these intermediates is carried out in order to generate hexaoxa(6)peristylane as well as diphenylhexaoxa[6]peristylane. Molecular modeling studies, performed at the semi-empirical level, are also described.