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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.

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Metadaten
Author:Bagrat A. Shainyan, Svetlana V. Kirpichenko, Erich Kleinpeter
DOI:https://doi.org/10.1016/j.tet.2012.05.106
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2012
Year of Completion: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
Pagenumber:8
First Page:7494
Last Page:7501
Funder:Russian Foundation for Basic Research; Deutsche Forschungsgemeinschaft [11-03-91334]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert