Analysis of the nuclear magnetic resonance spectra of 2-substituted 1,3-oxathiolanes. Determination of the conformation of the oxathiolane ring system and the conformational free energy values for the 2-alkyl substituents

1967 ◽  
Vol 89 (17) ◽  
pp. 4368-4374 ◽  
Author(s):  
Daniel J. Pasto ◽  
Francis M. Klein ◽  
Terrence W. Doyle
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Free Energy ◽  
Magnetic Resonance ◽  
Ring System ◽  
Nuclear Magnetic Resonance Spectra ◽  
Conformational Free Energy ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

5-Nitro-6-substituted-2-norbornenes: determination of Diels-Alder isomer ratios from nuclear magnetic resonance spectra

1967 ◽  
Vol 45 (23) ◽  
pp. 2969-2978 ◽  
Author(s):  
Wayland E. Noland ◽  
Bruce A. Langager ◽  
Joseph W. Manthey ◽  
Anthony G. Zacchei ◽  
Darryl L. Petrak ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Nuclear Magnetic Resonance Spectra ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The nuclear magnetic resonance spectra of representative 5-nitro-6-substituted-2-norbornenes (II–VII) are described. From the spectra, ratios of the two possible endo–exo trans stereoisomers derived from the Diels–Alder reaction of cyclopentadiene with the appropriate trans nitroölefin are estimated as shown in Table II. For all cases, there was predominance (3:1 to 9:1) of the 5-endo-nitro trans stereoisomer. The synthesis of the 6-(p-nitrophenyl) (V), 6-(2-furyl) (VI), and 6-(2-thienyl) (VII) derivatives is reported and the 6-ethyl derivative (III) has been characterized

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