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Synthesis, molecular structure, conformational analysis, and chemical properties of silicon-containing derivatives of quinolizidine

  • A silicon analog of quinolizidine 3,3,7,7-tetramethylhexahydro-1H-[1,4,2]oxazasilino[4,5-d][1,4,2]oxazasilin-9a-yl)methanol 3 was synthesized. X-ray diffraction analysis confirmed the trans configuration and low temperature NMR spectroscopy both the flexibility (barrier of interconversion 5.8 kcal mol(-1)) and the conformational equilibrium (chair-chair and chair-twist conformers) of the compound. The relative stability of the different isomers/conformers of 3 was calculated also at the MP2/6-311G(d,p) level of theory. Intra- and intermolecular hydrogen bonding in 3 and the appropriate equilibrium between free and self-associated molecules was studied in solvents of different polarity. Both the N-methyl quaternary ammonium salt and the O-trimethylsilyl derivative of 3 could be obtained and their structure determined.

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Metadaten
Author:Nataliya F. Lazareva, Bagrat A. Shainyan, Uwe SchildeORCiDGND, Nina N. Chipanina, Larisa P. Oznobikhina, Alexander I. Albanov, Erich Kleinpeter
DOI:https://doi.org/10.1021/jo202658n
ISSN:0022-3263 (print)
Parent Title (English):The journal of organic chemistry
Publisher:American Chemical Society
Place of publication:Washington
Document Type:Article
Language:English
Year of first Publication:2012
Year of Completion:2012
Release Date:2017/03/26
Volume:77
Issue:5
Pagenumber:7
First Page:2382
Last Page:2388
Funder:Russian Foundation for Basic Research; Deutsche Forschungsgemeinschaft [11-03-91334]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert