Date of Award
Honors Thesis (Open Access)
Colby College. Chemistry Dept.
Dasan M. Thamattoor
D. Whitney King
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 hexaoxaperistylane 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 diphenylhexaoxaperistylane. Molecular modeling studies, performed at the semi-empirical level, are also described.
Hydrocarbons -- Synthesis, Organic compounds -- Synthesis, Oxidation
Recommended CitationOtte, Douglas Arthur, "Synthetic approach to hexaoxaperistylanes. A novel DDQ-induced oxidative rearrangement" (2001). Honors Theses. Paper 192.
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