Year
1970
Degree Name
Bachelor of Science (Hons.)
Department
Department of Chemistry
Recommended Citation
Worth, Brian Robert, Phenanthropiperidines and related compounds, Bachelor of Science (Hons.) thesis, Department of Chemistry, University of Wollongong, 1970. https://ro.uow.edu.au/theses/898
Abstract
Syntheses of variously substituted diphenylpiperidine derivatives were accomplished and their reactions, as intermediates in a new synthetic route to the physiologically active phenanthroindolizidine alkaloids and their analogues, were investigated. The s5nithesis involves Michael addition of phenylacetonitrile donors to ethyl cinnamate acceptors, yielding a series of ethyl-3,4-diphenyl-4-cyanobutanoates bearing aromatic methoxy, methylenedioxy and iodo substituents. Reductive cyclisation of these cyanoesters with Raney-nickel or copper chromite catalysts gave, imder exactly controlled conditions, either secondary or tertiary diphenylpiperidine derivatives or the corresponding dC - lactams. The ratio of the cis- and trans- racemates formed in each reaction was found to vary with changes in reduction temperature and with the substituent pattern of the starting material.
Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong.