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Optica Publishing Group
  • Applied Spectroscopy
  • Vol. 22,
  • Issue 3,
  • pp. 204-205
  • (1968)

Differentiation of Cis-Trans Configurations of Trialkylethylene Isomers by Infrared Spectroscopy

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Abstract

A method for the detection and identification of <i>cis-trans</i> isomers of trialkyl ethylenes has not been established. Greenlee and Wiley, Hively, and Rummens, have attempted to develop methods that employ boiling-point differences, gas-chromatographic retention times, and rehybridization concepts, respectively. Corish has developed a method that employs an absorption band near 4065 cm<sup>−1</sup> to determine the <i>cis</i> content in polyisoprenes. We have investigated the near- and middle-infrared regions in an attempt to relate absorption bands that are produced by <i>cis-trans</i> polyisoprenes to bands produced by isomers of other similar trialkylethylene structures. In our study, the R<sub>1</sub>–CH=C CH<sub>3</sub>R<sub>2</sub> structures were investigated where R<sub>1</sub> is an alkyl group and R<sub>2</sub> is an alkyl substituent other than a methyl group. The Rule 10.11 of IUPAC <i>Notation for Organic Compounds,</i> has been used for the <i>cis-trans</i> nomenclature. This consists of designating the compounds with the two longest chains on the same side of the double bond as being in the <i>cis,</i> and on opposite sides of the double bond as being in the <i>trans</i> configurations.

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