4-Aziadamantan-1-amine: Synthesis, reactions and cyclodextrin complexes
- Author(s)
- Wolfgang Knoll, Michael Bobek, Gerald Giester, Udo H. Brinker
- Abstract
A new and potentially therapeutic diazirine, 4-aziadamantan-1-amine, was synthesized. Structural characterization also included single crystal X-ray diffraction analysis. Photolysis of the title compound in the solid phase afforded an azine. In contrast, pyrolysis in the gas phase gave two intramolecular carbene insertion products in a 4:1 ratio. A rationale for the observed diastereoselectivity is offered based upon ab initio calculations. Finally, inclusion compounds of the title compound with a- and ß-cyclodextrin were prepared. A 2:1 complex bearing two hosts was formed with a-cyclodextrin and a 1:1 complex was obtained with ß-cyclodextrin. The association constants were determined via induced circular dichroism (ICD) analysis. Œ 2001 Elsevier Science Ltd. All rights reserved.
- Organisation(s)
- Department of Organic Chemistry, Department of Mineralogy and Crystallography
- External organisation(s)
- University of Vienna
- Journal
- Tetrahedron Letters
- Volume
- 42
- Pages
- 9161-9165
- No. of pages
- 5
- ISSN
- 0040-4039
- DOI
- https://doi.org/10.1016/S0040-4039(01)02013-5
- Publication date
- 2001
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 1051 Geology, Mineralogy
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/b8279bbd-5c08-4080-90fe-d3265d39b854