13 C nuclear magnetic resonance spectroscopic analysis of the triacylglycerol composition ofBiota orientalis and carrot seed oil

1996 ◽  
Vol 73 (5) ◽  
pp. 557-562 ◽  
Author(s):  
Marcel S. F. Lie Ken Jie ◽  
C. C. Lam ◽  
Mohammed Khysar Pasha
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Seed Oil ◽  
Spectroscopic Analysis ◽  
Triacylglycerol Composition ◽  
Carrot Seed ◽  
Magnetic Resonance Spectroscopic Analysis ◽  
Nuclear Magnetic

Stereochemistry of acid-catalyzed cleavage of 7-chloro-1-methylnortricyclene in deuterated medium; evidence for edge protonation of nortricyclenes

1980 ◽  
Vol 58 (16) ◽  
pp. 1725-1737 ◽  
Author(s):  
Nick Henry Werstiuk ◽  
Frank Peter Cappelli
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Spectroscopic Analysis ◽  
Methyl Group ◽  
Magnetic Resonance Spectroscopic Analysis ◽  
Acid Catalyzed ◽  
Nuclear Magnetic

Cleavage of 7-chloro-1-methylnortricyclene (1e) in D2SO4–DOAc yields deuterated syn-7-chloro-1-methyl-exo-2-norbornyl acetate (3a-d) (1.04 excess d per molecule) and deuterated anti-7-chloro-1-methy l-exo-2-norbornyl acetate (3b-d) (1.28 excess d per molecule) as the kinetic products. 1H and 2H nuclear magnetic resonance spectroscopic analysis of the corresponding alcohols complexed with Eu(fod)3 shows that deuterium is located endo at C-6 and in the methyl group of the syn-7-chloroacetate, endo at C-6 and C-2, at C-7, and in the methyl group of the anti-7-chloroacetate. That the deuterium at C-6 of both acetates is 80–90% stereochemically pure endo, in our view, establishes that the bond farthest removed from the electron-withdrawing chlorine is preferentially cleaved via edge deuteronation.

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