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Updated: Apr 19, 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
The cyclopentyl group, as a small but bulky terminal group, allows rapid and efficient active transport
Junya Nishiyama1, Yoshimasa Makita, Nobuhiro Kihara
1Department of Chemistry, Faculty of Science, Kanagawa University , 2946 Tsuchiya, Hiratsuka 259-1293, Japan.
Abstract:
Secondary ammonium salts bearing a cyclopentyl terminal group rapidly formed pseudorotaxane with 1.5 equiv of DB24C8. Acylation of the pseudorotaxane with 50 equiv of benzoyl chloride in the presence of 50 equiv of triethylamine in toluene afforded rotaxane, the product of active transport, in 95% yield. The cyclopentyl group is small enough to allow rapid formation of pseudorotaxane, and bulky enough to facilitate the quantitative active transport by steric repulsion.
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