Abstract

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.

Degree

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

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