title: The cyclopentyl group, as a small but bulky terminal group, allows rapid and efficient active transport.
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.
authors.affiliation: Department of Chemistry, Faculty of Science, Kanagawa University , 2946 Tsuchiya, Hiratsuka 259-1293, Japan.
authors.forename: Junya
authors.initials: J
authors.lastname: Nishiyama
authors.forename: Yoshimasa
authors.initials: Y
authors.lastname: Makita
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Kihara
mesh_terms: D000215:Acylation; D001693:Biological Transport, Active; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D043862:Rotaxanes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D003517:Cyclopentanes; D043862:Rotaxanes