Hydride reductions of a-cyanobromolycopodine and simple derivatives provided a number of derivatives of these compounds useful for oxidation and dehydrogenation studies. Dehydrogenation of a-des-tetrahydrolycrodine yielded a
quinoline derivative. This result together with other evidence indicated that three of the four rings of lycopodine are six-membered. Two conjugated enols were isolated from oxidation experiments on a -cyanlyopodine. This indicated the presence of an active methylene group and from examination of these enols it appears unlikely that the carbonyl and nitrogen can be in the same ring. A benzal derivative was prepared from a-cyanolycopodine. This derivative was converted into a tertiary base which under-went a bond scission reaction with methyl sulfate. A selenium dioxide oxidation product of benzal-a -cyanolyco-podine gave some indication of the relationship of the carbonyl to the nitrogen in lycopodlne. / Thesis / Doctor of Philosophy (PhD)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/25549 |
| Date | 09 1900 |
| Creators | Barclay, Lawrence |
| Contributors | MacLean, D.B., Chemistry |
| Source Sets | McMaster University |
| Language | English |
| Detected Language | English |
| Type | Thesis |
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