High resolution 13C NMR spectroscopy. IV—stereochemical assignments in butenedioic acids and 3‐pentene‐2‐ones
Author:
- 14 April 1978
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 11 (4) , 197-203
Abstract
Vicinal 13C, H coupling constants 3J(CO, H) for butenedioic acids and 3J(CH3, H) for 3‐pentene‐2‐ones have been determined and are correlated with the configuration of the corresponding CC double bond. For both types the relationship 3J(CH) trans > 3J(CH)cis holds; in the case of the CH3, H couplings, however, the 3J(CH3, H) trans values are reduced because of steric reasons, so that configurational assignments seem possible only when both isomers are present. Additionally, the coupling constants 3J(COCH3,H) and the chemical shifts δ have been evaluated for the pentenones and it is shown that these parameters give information about the predominating conformation of α, β‐unsaturated methyl ketones.Keywords
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