Abstract
The cyclo-oligomerization of several terminal and internal alkynes under phase transfer conditions by the RhCl 3-Aliquat® 336 catalyst is described. The kinetics of 1-heptyne cyclotrimerization at 90 °C in 1,1,2,2-tetrachloroethane/water were found to follow the second-order rate law d[arene]/d t = − k[alkyne][RhCl 3] when the molar ratio of substrate:rhodium chloride:quat was approximately 25:1:1. The activation energy of E a = 12.5 kcal mol −1 suggests that the catalysis is both chemically and diffusion controlled. Product analysis is compatible with a mechanism that involves rhodacyclopentadiene rather than metal cyclobutadiene intermediates.
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