Improvement and Characterization Studies on the Intramolecular Azidodiene to Pyrrolizidine Cycloaddiction Reaction
Preston, Janine K.
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1, 3 dipolar cycloadditions have been recognized as facile methods of preparing bicyclic molecules. This has proven especially useful with naturally occurring compounds. In order to complete our target pyrrolizidine ring system, which is present in many biologically active molecules, it was first necessary to substitute a heptadiene in the 3-position so that the cycloadduct would have the proper functional groups placed in position prior to the cycloaddition. Selenium was chosen as the substituted heteroatom due to its Group VI periodic chart characteristics. The selenyl-substituted diene is converted into the azide which then undergoes the intramolecular cycloaddition in a very short period of time. A supplementary part of the project involved finding the best method of substitution of heteroatoms onto the diene and obtaining the optimum reaction conditions. Phosphorous compounds as well as selenium were explored.