Diastereomeric solute-solute interactions of enantiomers in achiral solvents. Nonequivalence of the nuclear magnetic resonance spectra of racemic and optically active dihydroquinine

1969 ◽  
Vol 91 (7) ◽  
pp. 1871-1872 ◽  
Author(s):  
Thomas Williams ◽  
R. G. Pitcher ◽  
P. Bommer ◽  
J. Gutzwiller ◽  
M. Uskokovic
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Optically Active ◽  
Nuclear Magnetic Resonance Spectra ◽  
Solute Interactions ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

Diastereoisomeric 2-aryl-6-methyl-3,4 (1,2-piperido)-oxazines

1968 ◽  
Vol 46 (7) ◽  
pp. 1105-1111 ◽  
Author(s):  
G. A. Cooke ◽  
G. Fodor
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Catalytic Hydrogenation ◽  
Optically Active ◽  
The Other ◽  
Nuclear Magnetic Resonance Spectra ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The alkaloid sedridine (1) is formed stereospecifically by catalytic hydrogenation of optically active α-picolyl methyl carbinol (2). The levorotatory 1 gave on action of p-nitro benzaldehyde two μ-aryl oxazines, one crystalline and levorotatory, the other oily and dextrorotatory. This is the first example where both epimers of a μ-aryl oxazine could be detected. The configurations and the conformations of these isomers (10 and 11) and those of sedridine have been discussed in terms of their nuclear magnetic resonance spectra, with particular reference to spin-decoupling evidence.

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