The Nonequivalence of Physical Properties of Enantiomers in Optically Active Solvents. Differences in Nuclear Magnetic Resonance Spectra. I

1966 ◽  
Vol 88 (8) ◽  
pp. 1837-1837 ◽  
Author(s):  
W. H. Pirkle
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Physical Properties ◽  
Optically Active ◽  
Nuclear Magnetic Resonance Spectra ◽  
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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