Convenient and Efficient Tosylation of Oligoethylene Glycols and the Related Alcohols in Tetrahydrofuran–Water in the Presence of Sodium Hydroxide

Ouchi, Mikio; Inoue, Yoshihisa; Liu, Yu; Nagamune, Satoshi; Nakamura, Satoko; Wada, Kazuhito; Hakushi, Tadao

doi:10.1246/bcsj.63.1260

Cited by 127 publications

(75 citation statements)

References 13 publications

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“…The tosyloxymethyl derivative of the 15-crown-5-ether was synthesized from hydroxymethyl-15-crown-5 and p-toluenesulfonyl chloride according to the procedure described in the literature 9,10 . Condensation of hydroxyl derivatives and tosylated 15-crown-5-carbinol proceeded for 3 days in DMF in the presence of NaH at 60 o C. The raw products 1 and 2 were purified by column chromatography on a silica gel with 72 and 37% yield, respectively.…”

Section: Resultsmentioning

confidence: 99%

New bis(15-crown-5) derivatives and their physicochemical properties

Kuś¹

2010

Arkivoc

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Dedicated to Professor Richard A. Bartsch on the occasion of his 70 th birthday AbstractTwo novel bis-crown ethers 1 and 2 were obtained. Both compounds form complexes with alkali metal ions. Such formation process was investigated using mass spectrometry (ESI MS). Compounds 1 and 2 can form both mono-and bimetallic complexes. Detected also are ions that reflect formation of complexes between two molecules of bis-crown ethers and one metal ion. Cesium and rubidium ions form with compound 2 only complexes of 1:1 type.

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Section: Resultsmentioning

confidence: 99%

New bis(15-crown-5) derivatives and their physicochemical properties

Kuś¹

2010

Arkivoc

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“…[16] Reagents were purchased from Aldrich except for 1´4 PF 6 , [17] 3, [18] 6, [19] [21] which were synthesised according to literature procedures. Thin-layer chromatography (TLC) was carried out with aluminium sheets, precoated with silica gel 60F (Merck 5554) or aluminium oxide 60F 254 neutral (Merck 5550).…”

Section: Methodsmentioning

confidence: 99%

Photoactive Azobenzene-Containing Supramolecular Complexes and Related Interlocked Molecular Compounds

Asakawa¹,

Ashton²,

Balzani³

et al. 1999

Chem. Eur. J.

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Two acyclic and three macrocyclic polyethers, three [2]catenanes, and one [2]rotaxane, each containing one 4,4'-azobiphenoxy unit, have been synthesized. In solution, the azobenzene-based acyclic polyethers are bound by cyclobis(paraquat-p-phenylene)Ða tetracationic cyclophaneÐin their trans forms only. On irradiation (l 360 nm) of an equimolar solution of the tetracationic cyclophane host and one of the guests containing a trans-4,4'-azobiphenoxy unit, the trans double bond isomerizes to its cis form and the supramolecular complex dissociates into its molecular components. The trans isomer of the guest and, as a result, the complex are reformed, either by irradiation (l 440 nm) or by warming the solution in the dark. Variable temperature 1 H NMR spectroscopic investigations of the [2]catenanes and the [2]rotaxane revealed that, in all cases, the 4,4'-azobiphenoxy unit resides preferentially alongside the cavities of their tetracationic cyclophane components, which are occupied either by a 1,4-dioxybenzene or by a 1,5-dioxynaphthalene unit. In the acyclic and macrocyclic polyethers containing 1,4-dioxybenzene or 1,5-dioxynaphthalene chromophoric groups and a 4,4'-azobiphenoxy moiety, the fluorescence of the former units is quenched by the latter. Fluorescence quenching is accompanied by photosensitization of the isomerization. The rate of the energy-transfer process is different for trans and cis isomers. In the [2]rotaxane and the [2]catenanes, the photoisomerization is quenched to an extent that depends on the specific structure of the compound. Only in one of the three [2]catenanes and in the [2]rotaxane was an efficient photoisomerization (l 360 nm) from the trans to the cis isomer of the 4,4'-azobiphenoxy unit observed. Single crystal X-ray structural analysis of one of the [2]catenanes showed that, in the solid state, the 4,4'-azobiphenoxy unit in the macrocyclic polyether component also resides exclusively alongside. The cavity of the tetracationic cyclophane component of the [2]catenane is filled by a 1,5-dioxynaphthalene unit, and infinite donor ± acceptor stacks between adjacent [2]catenanes are formed in the crystal. These supramolecular complexes and their mechanically interlocked molecular counterparts can be regarded as potential photoactive nanoscale devices.

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“…5a Later, the selective direct ditritylation of SPM to produce 10a was reported. 8 On the other hand, bisacylation of 1,8-diaminooctane (DAO), followed by LiAlH 4 reduction of the bisamide 9b produced the N 1 ,N 16 -ditritylated tetra-amine 10b in 61% yield. 4 Similarly, bisacylation of PUT with SAE 6 produced the tetra-amide 11 in 82% yield.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of crowned polyamines using isolable succinimidyl esters of N-tritylated linear amino acids and peptides

Tsiakopoulos¹,

Damianakos²,

Vahliotis³

et al. 2003

Arkivoc

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Partial and total syntheses of polyamines incorporating crown ether moieties have been effected using N-tritylated linear amino acids, like β-alanine (βAla) and γ-aminobutyric acid (γAba), to introduce the N-3-C and N-4-C polyamine structural units, respectively. The partial syntheses involve the acylation of commercially available crown bearing amino function(s) or aza-oxa crown ethers with the isolable succinimidyl esters of Trt-βAla-OH or Trt-βAla-γAba-OH, followed by LiAlH 4 -mediated reduction of the resulting amides, whereas in the total syntheses the crown and the aza-oxa crown ether moieties are built-up from commercially available starting materials like polyethylene glycols, epichlorohydrin and dibenzylamine.

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Convenient and Efficient Tosylation of Oligoethylene Glycols and the Related Alcohols in Tetrahydrofuran–Water in the Presence of Sodium Hydroxide

Cited by 127 publications

References 13 publications

New bis(15-crown-5) derivatives and their physicochemical properties

New bis(15-crown-5) derivatives and their physicochemical properties

Photoactive Azobenzene-Containing Supramolecular Complexes and Related Interlocked Molecular Compounds

Syntheses of crowned polyamines using isolable succinimidyl esters of N-tritylated linear amino acids and peptides

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