Fluorinated carbohydrates. Part V. Nuclear magnetic resonance data on pyranose and furanose derivatives of 3-deoxy-3-fluoro-D-glucose

1970 ◽  
Vol 48 (24) ◽  
pp. 3937-3945 ◽  
Author(s):  
A. B. Foster ◽  
R. Hems ◽  
L. D. Hall
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Nuclear Magnetic Resonance Data ◽  
Spectral Parameters ◽  
Magnetic Resonance Data ◽  
Resonance Data ◽  
Derivatives Of ◽  
Glucose Derivatives ◽  
Nuclear Magnetic

The n.m.r. spectra of a series of 3-fluorinated glucose derivatives have been measured; spectral assignments were confirmed by 1H–{19F} heteronuclear decoupling experiments. The 19F spectral parameters illustrate a variety of stereospecific dependencies, the most noteworthy being that of 4JF,H couplings, for which 4Je,e = ca. + 4.0 Hz while 4Je,a = ca. − 1.5 Hz.

NEW REARRANGEMENTS OF THE CARYOPHYLLENE SKELETON: THE DINITROPHENYLHYDRAZONES FROM CARYOPHYLLENE OXIDE

1964 ◽  
Vol 42 (7) ◽  
pp. 1664-1675 ◽  
Author(s):  
E. W. Warnhoff
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Nuclear Magnetic Resonance Data ◽  
Chemical Data ◽  
Caryophyllene Oxide ◽  
Magnetic Resonance Data ◽  
Resonance Data ◽  
Derivatives Of ◽  
Nuclear Magnetic

Caryophyllene oxide (I) and dihydrocaryophyllene oxide (II) have been found to give 2,4-dinitrophenylhydrazones. Structures IV, V, and VII are assigned to three of these compounds on the basis of nuclear magnetic resonance data, other spectral and chemical data, and mechanistic considerations. Structure VII is the product of a new cyclization–rearrangement of the caryophyllene system. The dinitrophenylhydrazone previously obtained from isocaryophyllene oxide-a (III) is probably identical with VII. Three other new derivatives of caryophyllene are described, one of which (VI) is an intermediate in the conversion of I to VII.

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