Synthesis and characterization of stereospecific 1-propargyl-2-(dimethoxymethyl)-1-cyclohexanols

Stereochemical isomers with hydroxy groups were synthesized by reacting 2-(dimethoxymethyl)cyclohexanone with propargylmagnesium bromide. The stereo chemical structures were identified by NMR spectral interpretation and the geometry optimization. To assist the NMR interpretation, geometry optimizati...

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Bibliographic Details
Published in:Archives of pharmacal research 2000-04, Vol.23 (2), p.104-111
Main Authors: Liu, J, Kim, S I, Lee, S Y, Kim, Y H, Lee, K Y, Oh, C Y, Ham, W H
Format: Article
Language:English
Subjects:
Alkynes - chemical synthesis
Alkynes - chemistry
Indicators and Reagents
Isomerism
Magnetic Resonance Spectroscopy
Molecular Conformation
Propanols - chemical synthesis
Propanols - chemistry
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Summary:Stereochemical isomers with hydroxy groups were synthesized by reacting 2-(dimethoxymethyl)cyclohexanone with propargylmagnesium bromide. The stereo chemical structures were identified by NMR spectral interpretation and the geometry optimization. To assist the NMR interpretation, geometry optimization based on semi-empirical AM1 and PM3 methods was applied. Throughout this study, the structures of the two isomers were all determined and 1H and 13C NMR spectra were fully assigned. It was proven that the less polar isomer is an axial alcohol and the more polar one is an equatorial alcohol.
ISSN:0253-6269
1976-3786
DOI:10.1007/BF02975497