Sequence-Selective Synthesis of Rotacatenane Isomers

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

doi:10.1021/acs.joc.5b02697

Sequence-Selective Synthesis of Rotacatenane Isomers

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

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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 (1)H and (13)C NMR spectroscopy.

Original language	English
Pages (from-to)	1175-84
Number of pages	10
Journal	The Journal of organic chemistry
Volume	81
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.5b02697
Publication status	Published - 7 Jan 2016

Keywords

Journal Article
Research Support, Non-U.S. Gov't

Access to Document

10.1021/acs.joc.5b02697

Cite this

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title = "Sequence-Selective Synthesis of Rotacatenane Isomers",

abstract = "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 (1)H and (13)C NMR spectroscopy. ",

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author = "Ryuto Hayashi and Petr Slav{\'i}k and Yuichiro Mutoh and Takeshi Kasama and Shinichi Saito",

year = "2016",

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T1 - Sequence-Selective Synthesis of Rotacatenane Isomers

AU - Hayashi, Ryuto

AU - Slavík, Petr

AU - Mutoh, Yuichiro

AU - Kasama, Takeshi

AU - Saito, Shinichi

PY - 2016/1/7

Y1 - 2016/1/7

N2 - 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 (1)H and (13)C NMR spectroscopy.

AB - 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 (1)H and (13)C NMR spectroscopy.

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1021/acs.joc.5b02697

DO - 10.1021/acs.joc.5b02697

M3 - Article

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SN - 0022-3263

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JO - The Journal of organic chemistry

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