Oligomerization of alkynes by the RhCl3-aliquat 336 catalyst system. Part 1. Formation of benzene derivatives

Ibrahim Amer*, Tamar Bernstein, Moris Eisen, Jochanan Blum, K. Peter C. Vollhardt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

The cyclo-oligomerization of several terminal and internal alkynes under phase transfer conditions by the RhCl3-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]/dt = -k[alkyne][RhCl3] when the molar ratio of substrate:rhodium chloride:quat was approximately 25:1:1. The activation energy of Ea = 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.

Original languageEnglish
Pages (from-to)313-321
Number of pages9
JournalJournal of Molecular Catalysis
Volume60
Issue number3
DOIs
StatePublished - 1 Jul 1990
Externally publishedYes

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