@article{LazarevaShainyanSchildeetal.2012, author = {Lazareva, Nataliya F. and Shainyan, Bagrat A. and Schilde, Uwe and Chipanina, Nina N. and Oznobikhina, Larisa P. and Albanov, Alexander I. and Kleinpeter, Erich}, title = {Synthesis, molecular structure, conformational analysis, and chemical properties of silicon-containing derivatives of quinolizidine}, series = {The journal of organic chemistry}, volume = {77}, journal = {The journal of organic chemistry}, number = {5}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo202658n}, pages = {2382 -- 2388}, year = {2012}, abstract = {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.}, language = {en} }