TY  - JOUR
A1  - Lazareva, Nataliya F.
A1  - Shainyan, Bagrat A.
A1  - Schilde, Uwe
A1  - Chipanina, Nina N.
A1  - Oznobikhina, Larisa P.
A1  - Albanov, Alexander I.
A1  - Kleinpeter, Erich
T1  - Synthesis, molecular structure, conformational analysis, and chemical properties of silicon-containing derivatives of quinolizidine
T2  - The journal of organic chemistry
N2  - 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.
Y1  - 2012
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/36047
SN  - 0022-3263
VL  - 77
IS  - 5
SP  - 2382
EP  - 2388
PB  - American Chemical Society
CY  - Washington
ER  -