High Yielding and Practical Synthesis of Rotaxanes by Acylative End-Capping Catalyzed by Tributylphosphine

Kawasaki, Hiroaki; Kihara, Nobuhiro; Takata, Toshikazu

doi:10.1246/cl.1999.1015

Cited by 85 publications

(55 citation statements)

References 11 publications

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“…For 8 (Figure 1c), a signal originating from N-benzyl protons around the ammonium moiety appears as a broad peak because of geminal coupling, strongly supporting the formation of rotaxane in accordance with the literatures. 47,48 In addition, the observed methyl signal supports the formation of boron pinacolate of 8. The other signals are consistent with the structure of 8.…”

Section: Synthesis Of Poly(crown Ether)smentioning

confidence: 59%

Polymer architectures assisted by dynamic covalent bonds: synthesis and properties of boronate-functionalized polyrotaxane and graft polyrotaxane

Koyama

Suzuki

Asakawa

et al. 2011

Polym J

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Poly [2]rotaxane and graft polyrotaxane were synthesized from a mixture of poly(crown ether) (polyester-10 and polyisoxazole-13) as a trunk polymer, boronic-acid-terminated secondary ammonium salt 5 as an axle component, and diol as an end-capping group by pseudorotaxane formation and subsequent catalyst-free dehydrative bondage between the boronic acid and the diol moieties. Trunk polymers 10 and 13 were prepared by copolymerization of diol-or diyne-substituted dibenzo-24-crown-8-ether 9 or 11 and ditopic comonomers such as bifunctional acid dichloride and nitrile N-oxide. The use of the sufficiently bulky and stable homoditopic nitrile N-oxide 12 gave the high-molecular-weight isoxazole-containing poly(crown ether) 13 efficiently and without accidental penetration of the propagation end into the crown cavity, which would have caused gelation. The treatment of these poly(crown ether)s with boronic acid 5 in CH 2 Cl 2 gave the corresponding polypseudorotaxanes, and subsequent graftonto reaction with pinacol and a polymeric terminal diol gave poly[2]rotaxane and graft polyrotaxane. The chemical stability of these supramolecular architectures primarily depends on the bulkiness of the diol group as the end-capping moiety and the inherence originating from the dynamic covalent bond of boronate, as determined by detailed 1 H nuclear magnetic resonance study of model [2]rotaxanes 6-8 and the dissociation behavior of the polymers.

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Section: Synthesis Of Poly(crown Ether)smentioning

confidence: 59%

Polymer architectures assisted by dynamic covalent bonds: synthesis and properties of boronate-functionalized polyrotaxane and graft polyrotaxane

Koyama

Suzuki

Asakawa

et al. 2011

Polym J

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“…MS spectra were recorded with a JEOL JMS-700 spectrometer. Preparative chemical yield [31][32][33][34][35] than before [36]. Covalent methods [37], which were not thought to be versatile for the synthesis of interlocked molecules, were also well developed [38,39].…”

Section: Methodsmentioning

confidence: 99%

The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–

et al. 2018

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Rotaxanes consisting of achiral axle and achiral ring components can possess supramolecular chirality due to their unique geometrical architectures. To synthesize such chiral rotaxanes, we adapted a prerotaxane method based on aminolysis of a metacyclophane type prerotaxane that had planar chirality, which is composed of an achiral stopper unit and a crown ether type ring component. The prerotaxanes were well resolved using chiral HPLC into a pair of enantiomerically pure prerotaxanes, which were transferred into corresponding chiral rotaxanes, respectively. Obtained chiral rotaxanes were revealed to have considerable enantioselectivity.

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“…Thus, a series of [2]rotaxanes (223a-d) were synthesized from dibenzo-24-crown-8 (224) and dibenzylammonium salts (225a-d) under catalysis by Bu 3 P (Scheme 48). [113][114][115] When a catalyst is a strong acid, e.g. triflic acid, the corresponding amine can be used as a base, since ammonium salts can be produced in sutu.…”

Section: Nn'n''n'''-tetrasubstituted Cyclam (195) Synthesised Frommentioning

confidence: 99%

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

Ishmuratov¹,

Yakovleva²,

Выдрина³

et al. 2017

MHC

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High Yielding and Practical Synthesis of Rotaxanes by Acylative End-Capping Catalyzed by Tributylphosphine

Cited by 85 publications

References 11 publications

Polymer architectures assisted by dynamic covalent bonds: synthesis and properties of boronate-functionalized polyrotaxane and graft polyrotaxane

Polymer architectures assisted by dynamic covalent bonds: synthesis and properties of boronate-functionalized polyrotaxane and graft polyrotaxane

The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

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