Kinetics of pi-complex isomerization during AlCl3-catalyzed Friedel-Crafts reactions between linear olefins and p-xylene

Rapid isomerization of pi‐complex intermediates results in the formation of multiple isomers of alkyl aromatics during AlCl3‐catalyzed reactions between linear olefins and aromatic rings. The authors present results of a kinetic study of reactions between p‐xylene, 1‐dodecene, and linear tetradecenes. Product distributions are well predicted based on a model of reversible pi‐complex isomerization. Surprisingly, no double bond isomerization was observed in the linear olefins: All isomerization occurred in the pi‐complexes. Copyright © 2014 John Wiley & Sons, Ltd. A kinetic model of rapidly isomerizing pi‐complex intermediates explains the quantitative distribution of alkylate isomers observed during Friedel–Crafts reactions between p‐xylene and linear olefins. Double bond isomerization was not observed in the olefins.