Spectroscopic studies on olefins—III: NMR of <i>cis</i>‐ and <i>trans</i>‐ disubstituted olefins

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<jats:title>Abstract</jats:title><jats:p>The proton NMR spectra of four <jats:italic>cis</jats:italic>/<jats:italic>trans</jats:italic> pairs of 1,2‐disubstituted olefins have been analysed. The observed trends of the olefinic, vicinal and allylic proton‐proton coupling constants are discussed in terms of rehybridization at the <jats:italic>sp</jats:italic><jats:sup>2</jats:sup> carbon atoms. It is found that in these substances the <jats:italic>trans</jats:italic>‐allylic couplings are generally more negative than the <jats:italic>cis</jats:italic>‐allylic couplings contrary to Barfield's<jats:sup>1</jats:sup> theoretical prediction but in agreement with some earlier experimental data. Steric hindrance between <jats:italic>cisoid</jats:italic> substituents is cited as the probable origin of this end related trends.</jats:p>

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