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http://hdl.handle.net/11375/25549
Title: | The Chemistry of Lycopodine |
Authors: | Barclay, Lawrence |
Advisor: | MacLean, D.B. |
Department: | Chemistry |
Keywords: | chemistry;lycopodine |
Publication Date: | Sep-1957 |
Abstract: | 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. |
URI: | http://hdl.handle.net/11375/25549 |
Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Barclay_Lawrence_R_1957Sep_PhD.pdf | 4.58 MB | Adobe PDF | View/Open |
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