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You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page. Issue 9, Previous Article Next Article. From the journal: Chemical Society Reviews. Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes. This article is part of the themed collection: Supramolecular chemistry anniversary.

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Back to tab navigation Download options Please wait Article type: Review Article. DOI: Download Citation: Chem. Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes Z.

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Liu, S. Nalluri and J. The aryl groups include phenyl, tolyl and naphthyl etc. The aryloxy groups include phenyloxy, tolyloxy and naphthyloxy etc. The alkylthio groups are desirably those in which the alkyl group has 1 to 4 carbon atoms, including methylthio, ethylthio and propylthio etc. The alkylsulfinyl groups are desirably those having 1 to 6 carbon atoms, including methylsulfinyl, ethylsulfinyl and propylsulfinyl etc. The ring A is not substituted or is substituted at the 4- or 5-position particularly desirably with alkyl, halogen, trifluoromethyl or alkoxy among the substituents described above.

The N-protective groups represented by R 1 include alkyl, acyl, carboalkoxy, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, alkylcarbonylmethyl, alkoxycarbonylmethyl and alkylsulfonyl etc. The alkyl groups are desirably those having 1 to 5 carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl and pentyl etc. The acyl groups include the same groups as those described for the substituents of the ring A. The carboalkoxy groups include the same groups as those described for the substituents of the ring A. The alkylcarbamoyl groups are represented by the formula: STR3 wherein the alkyl group has desirably 1 to 4 carbon atoms, including methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl and isopropylcarbamoyl etc.

The dialykylcarbamoyl groups are represented by the formula: STR4 wherein the alkyl groups have desirably 1 to 4 carbon atoms each, including dimethylcarbamoyl, diethylcarbamoyl and N-methyl-N-ethylcarbamoyl etc. The alkylcarbonylmethyl groups are represented by the formula: alkyl-COCH 2 -- wherein the alkyl group has desirably 1 to 4 carbon atoms, including acetylmethyl and propionylmethyl etc. The alkoxycarbonylmethyl groups are represented by the formula: alkyl-OCO-CH 2 -- wherein the alkyl group has desirably 1 to 4 carbon atoms, including methoxycarbonylmethyl, ethoxycarbonylmethyl and propoxycarbonylmethyl etc.

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Liquid crystalline crown ethers.

The alkylsulfonyl groups are represented by the formula: alkyl-SO 2 -- wherein the alkyl group has desirably 1 to 4 carbon atoms, including methylsulfonyl, ethylsulfonyl, propylsulfonyl and isopropylsulfonyl etc. The alkyl groups which may be fluorinated, represented by R 2 , R 3 and R 4 , have desirably 1 to 4 carbon atoms each.

Such unsubstituted alkyl groups include methyl, ethyl, propyl, isopropyl, butyl and isobutyl etc. Such fluorinated alkyl groups include trifluoromethyl, 2,2,2-trifluoroethyl, 2,2,3,3,3,-pentafluoropropyl, 1- trifluoromethyl -2,2,2-trifluoroethyl, 2,2,3,3-tetrafluoropropyl and 2,2,3,3,4,4,4-heptafluorobutyl etc.

The alkoxy groups which may be fluorinated, represented by R 2 , R 3 and R 4 , have desirably 1 to 8 carbon atoms each. Such unsubstituted alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, hexyloxy, heptyloxy and octyloxy. Such fluorinated alkoxy groups include 2,2,2-trifluoroethoxy, 2,2,3,3,3,-pentafluoropropoxy, 1- trifluoromethyl -2,2,2-trifluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 2,2,3,3,4,4,4-heptafluorobutoxy and 2,2,3,3,4,4,5,5-octafluoropentoxy.

In more detail about the compounds I and II , it is particularly desirable that the ring A is unsubstituted or substituted at the 4- or 5-position with methoxy or trifluoromethyl, R 1 is a hydrogen atom, R 2 and R 4 are independently hydrogen atom or methyl and R 3 is a fluorinated alkoxy having 2 to 5 carbon atoms. The amount of the vanadium compounds used is generally about 0. Hydrogen peroxide is usually used in an aqueous solution of hydrogen peroxide, but a solution in an organic solvent such as n-butylalcohol and a solution in the mixture of said organic solvent and water may also be used.

The amount of hydrogen peroxide used is usually a slight excess relative to one equivalent of the compound I , desirably about 1 to 3 equivalents, more desirably about 1 to 1. The solvents used for the reaction include halogenated hydrocarbons such as chloroform and dichloromethane, ethers such as tetrahydrofuran and dioxane, alcohols such as ethanol, methanol and isopropanol, ketones such as acetone and methylethylketone, nitriles such as acetonitrile and water, among which ethanol, methanol, acetone and acetonitrile are desirable and ethanol is more desirable.

These solvents may be used singly or in combination. The amount of the solvent used for the reaction is about 0. The desired compound II produced by the reaction described above is usually separated out as crystals from the reaction mixture, so that the crystals can be collected by filtration after decomposition of the excess of hydrogen peroxide remaining after the reaction by addition of an aqueous solution of sodium thiosulfate, but the crystals may also be collected by extraction with a solvent such as chloroform if necessary, followed by concentration.

The crystals thus collected can be purified if necessary by a routine method such as recrystallization and chromatography. The starting compounds I can be produced by the methods described in, for example, U. This invention is illustrated in more detail in the following Working Examples and Reference Example.

After completion of the reaction, an aqueous solution of sodium thiosulfate 0. The dichloromethane layer was washed with water 30 ml , and concentrated under reduced pressure; to the residue was added a mixture of ethanol-water , 10 ml for crystallization.

crown ether msc chemistry topic

This solution was ice-cooled, and the crystals were collected by filtration and washed with an ice-cooled mixture of ethanol-water The filtrate was ice-cooled for crystallization, and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture and dried in vacuo to give white crystals of 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylsulfinyl]benzimidazole 1.

The crystals were collected by filtration and washed with an ice-cooled mixture of ethanol-water The filtrate was ice-cooled for crystallization, and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture and dried in vacuo, to give white needles of 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylsulfinyl]benzimidazole 9. The filtrate was ice-cooled for crystallization, and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture and dried in vacuo, to give white needles of 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylsulfinyl]benzimidazole Vanadium IV acetylacetonate 40 mg was dissolved in ethanol ml , to which 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylthio]benzimidazole monohydrate After completion of the reaction, a solution of sodium thiosulfate 2.

The filtrate was ice-cooled for crystallization and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture and dried in vacuo, to give white needles of 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylsulfinyl]benzimidazole Each 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylsulfinyl]benzimidazole obtained in Examples and in Reference Example described below was analyzed by high performance liquid chromatography HPLC and the following results were obtained. Mobile phase: A mixture of methanol-water-triethylamine of which pH has been adjusted to 7.

According to the same method as in Example 4, the following compounds were produced and analyzed by HPLC under the same conditions as in Example 5; the results are summarized as follows. After completion of the reaction, the reaction mixture was washed with a solution of sodium hydrogencarbonate, and dried over magnesium sulfate, and chloroform was evaporated off under reduced pressure.

Liquid crystalline crown ethers.

To the residue was added ethanol ml for crystallization, which was ice-cooled; the resulting crystals were collected by filtration and washed with ice-cooled ethanol. The filtrate was ice-cooled for crystallization and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture , and dried in vacuo, to give white needles of 2-[[3-methyl 2,2,2-trifluoroethoxy pyridyl]methylsulfinyl]benzimidazole Year of fee payment : 4.

Year of fee payment : 8. Effective date : Year of fee payment : The reaction time is usually about 0. Tapeten We straight see in download ethers crown ethers hydroxyl groups and their sulphur analogues. All others are reviewed unless helped. This tops us allow you the black-and-white download ethers crown ethers hydroxyl groups and versions.

One-pot synthesis of novel thioxanthone crown ethers

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