The synthesis and stereochemical aspects of derivatives of the new ring system 2,6,10-triazatricyclo [5.2.1.04,10] decane are discussed. Sythesis of 2-nitro-2-methyl-1,3-disubstitutedaminopropanes, followed by reduction of these compounds to 2-amino-2-methyl-1,3-disubstituted aminopropanes afforded the necessary starting materials for a cyclization reaction similar to that resulting in already known 2,6-dioxa-10-azatricyclo [5.2.1.04,10] decanes. Reaction of the triamines with 2,5-hexanedione resulted in 2,6-disubstituted-1,4,7-trimethyl-2,6,10-triazatricyclo [5.2.1.04,10] decanes. The stereochemical aspects of this ring system are interesting from the standpoint of nitrogen inversion barriers on nitrogens 2 and 6. Existence of a high inversion barrier for these nitrogens in shown by isolation of different diastereomers of the tricycle. Methods used to show the presence of diastereomers are discussed.
| Identifer | oai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9209 |
| Date | 01 August 1975 |
| Creators | Foulger, Susan Elaine |
| Publisher | BYU ScholarsArchive |
| Source Sets | Brigham Young University |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Theses and Dissertations |
| Rights | http://lib.byu.edu/about/copyright/ |
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