Configurations and conformations in acyclic, unsaturated hydrocarbons. A 13C NMR study

J.W. Haan, de, L.J.M. Ven, van de

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Abstract

13C NMR (CMR) spectra of a number of di- and trisubstituted ethylenes have been measured. Very consistent values are found for the differential shieldings of allylic carbons in a number of linear, (Z)- and (E)-disubstituted ethylenes. The discrepancies between the several structural elements are explained tentatively by assuming different rotational preferences in the (Z)-isomers, the (E)-isomers, or both. The results obtained for some branched olefins are qualitatively in agreement with conclusions reached in previous 1H NMR (PMR) investigations, with the possible exception of 2,5-diMe-3-hexene. Differential shieldings in trisubstituted ethylenes are larger than in disubstituted ethylenes, probably as a consequence of steric interaction between geminal substituents. It is confirmed, that API's recent relabelling of the isomers of 3-Me-2-hexene was justified. Furthermore, the (E)-configuration is assigned to the high-boiling isomer of 3,4,4-triMe-2-pentene. On the other hand, the high-boiling isomer of 3-Et-4-Me-2-pentene is shown to be the (Z)-isomer. For the isomeric pair of geraniol and nerol, the (E)-configuration is assigned to the former and the (Z)-configuration to the latter, in agreement with our recent PMR investigations.
Original languageEnglish
Pages (from-to)147-153
Number of pages7
JournalOrganic Magnetic Resonance
Volume5
Issue number3
DOIs
Publication statusPublished - 1973

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