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

Volume 22, Number 3 (June 1968) Page 204-205

Clark, J.K.

A method for the detection and identification of cis-trans 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−1 to determine the cis content in polyisoprenes. We have investigated the near- and middle-infrared regions in an attempt to relate absorption bands that are produced by cis-trans polyisoprenes to bands produced by isomers of other similar trialkylethylene structures. In our study, the R1-CH=C CH3R2 structures were investigated where R1 is an alkyl group and R2 is an alkyl substituent other than a methyl group. The Rule 10.11 of IUPAC Notation for Organic Compounds, has been used for the cis-trans nomenclature. This consists of designating the compounds with the two longest chains on the same side of the double bond as being in the cis, and on opposite sides of the double bond as being in the trans configurations.