Synthesis and conformational analysis of 1,3-azasilinanes
- 1-Isopropyl-3-methyl-3-phenyl-1,3-azasilinane 1 and 1-isopropyl-3,3-dimethyl-1,3-azasilinane 2 were synthesized and a detailed analysis of their NMR spectra, conformational equilibria and ring inversion processes is presented. Low temperature H-1/C-13 NMR spectroscopy, iteration of the H-1 NMR spectra and quantum chemical calculations showed slight predominance of the PheqMeax over the PhaxMeeq conformer of 1 at low temperature. The barrier for the chair to chair interconversion of both compounds was measured to be 8.25 kcal/mol.
| Author details: | Bagrat A. Shainyan, Svetlana V. Kirpichenko, Erich KleinpeterORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1016/j.tet.2012.05.106 |
| ISSN: | 0040-4020 |
| Title of parent work (English): | Tetrahedron |
| Publisher: | Elsevier |
| Place of publishing: | Oxford |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2012 |
| Publication year: | 2012 |
| Release date: | 2017/03/26 |
| Tag: | 1,3-Azasilinanes; Conformational analysis; Dynamic NMR spectroscopy; Quantum chemical calculations; Ring current effect |
| Volume: | 68 |
| Issue: | 36 |
| Number of pages: | 8 |
| First page: | 7494 |
| Last Page: | 7501 |
| Funding institution: | Russian Foundation for Basic Research; Deutsche Forschungsgemeinschaft [11-03-91334] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
