Abstract
The stereochemical aspects of the cis-bicyclo[4.3.0]nona-3,7-diene epoxidation reaction by monoperoxyphthalic acid were investigated. The 1H and 13C NMR spectra of the stereoisomeric diepoxides obtained in this reaction have been studied experimentally and theoretically at the CSGT-PCM/PBE1PBE/6-31G ##(II) level. The application of combined experimental and theoretical NMR studies has allowed assignments of diepoxides to the corresponding stereoisomers to be made. The established trends of the influence of the orientation of the epoxide ring and the conformation of the bicyclic skeleton could be useful for stereochemical investigations of related polycyclic epoxidic compounds.
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