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Updated: Feb 23, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Functionalization of 3-Iridacyclopentenes
Margarita Gómez1, Nuria Rendón1, Eleuterio Álvarez1
1Instituto de Investigaciones Químicas, Departamento de Química Inorgánica, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Consejo Superior de Investigaciones Científicas (CSIC), Universidad de Sevilla, Avenida Américo Vespucio 49, 41092, Sevilla, Spain.
Abstract:
Members of a series of iridacyclopentenes of composition [TpMe2 Ir(k2 -C,C-CH2 CR'=CRCH2 )(CO)] (TpMe2 =hydrotris(3,5-dimethylpyrazolyl)borate; R=R'=H, 1; R=Me, R'=H, 2; R=R'=Me, 3) have been subjected to common organic chemistry procedures for hydrogenation, cyclopropanation, epoxidation, water addition through hydroboration, cis-dihydroxylation, and ozonolysis. The stability of metallacycles 1-3, imparted by the presence of the co-ligands TpMe2 and CO, directs the reactivity towards the C=C double bonds, and furthermore the stereochemistry of the products formed is strongly dictated by the steric demands of the TpMe2 ligand. While the products obtained in some of the above-mentioned reactions are the expected ones from an organic chemistry point of view, in other cases the results differ from the outcomes of similar reactions carried out with the all-carbon counterparts.
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