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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The isomerization of n-phenylbutenes catalysed by palladium complexes

NR Davies, AD DiMichiel and VA Pickles

Australian Journal of Chemistry 21(2) 385 - 395
Published: 1968

Abstract

4-Phenylbut-1-ene isomerizes to a mixture of cis- and trans-1-phenylbut-2-ene and trans-1-phenylbut-1-ene in the presence of bis(benzonitrile)dichloropalladium(11). The products are not formed entirely in consecutive reactions but direct conversion of 4-phenylbut-1-ene into trans-1-phenylbut-1-ene occurs extensively. Similarities are observed in the kinetics with those observed previously for allylbenzene. The isomerization of 1-phenylbut-2-ene to 1-phenylbut-1-ene is comparatively slow in spite of conjugation between the aromatic ring and the double bond in the side-chain within the latter compound. The rate-controlling step in the isomerization of 1-phenylbut-2-ene is believed to be an olefin displacement reaction, but an induction period renders the conclusions with regard to the kinetics of the initial isomerization of 4-phenylbut-1-ene less certain.

https://doi.org/10.1071/CH9680385

© CSIRO 1968

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