Sequence-selective synthesis of rotacatenane isomers

Ryuto Hayashi, Petr Slavík, Yuichiro Mutoh, Takeshi Kasama, Shinichi Saito

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Rotacatenane is an interlocked compound composed of two mechanically interlocked macrocyclic components, i.e., a [2]catenane, and one axle component. In this paper we describe the selective synthesis of isomeric rotacatenanes. Two [2]rotaxanes with different phenanthroline moieties were synthesized by the oxidative coupling of an alkyne with a bulky blocking group, which proceeded in the cavity of the macrocyclic phenanthroline-Cu complex. The metal template method was used to install another cyclic component: the tetrahedral Cu(I) complex, which was composed of a [2]rotaxane and an acyclic phenanthroline derivative, was synthesized, and the cyclization of the phenanthroline derivative gave the rotacatenane. The sequential isomers of rotacatenanes were distinguished by 1H and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)1175-1184
Number of pages10
JournalJournal of Organic Chemistry
Issue number3
Publication statusPublished - 5 Feb 2016

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