Chlorination of cellulose with N-chlorosuccinimide-triphenylphosphine under homogeneous conditions in lithium chloride-N,N-dimethylacetamide

Furuhata, Ken-ichi; Chang, Hu-Sheng; Aoki, Nobuyoshi; Sakamoto, Munenori

doi:10.1016/s0008-6215(00)90518-4

Cited by 39 publications

(28 citation statements)

References 27 publications

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“…The use of lithium halides/DMAc as a cellulose solvent in conjunction with another halogenating system (triphenylphosphine/N-halosuccinimides) produced high DS chlorodeoxy-(1.9) and bromodeoxycelluloses (0.9); however, degradation was still appreciable despite the DS's attained. This was reflected by a decrease in intrinsic viscosity of the insoluble (in 7 : 3 acetone : water) bromodeoxycellulose fraction from 2 to 0.8 and a corresponding decrease in the soluble bromdeoxycellulose fraction from 2 to 0.2 [20,21]. The mechanism of this reaction is similar to that observed with alcohols and carbohydrates and is shown in Fig.…”

Section: Halodeoxycellulosessupporting

confidence: 60%

Deoxycelluloses and related structures

Vigo¹,

Sachinvala²

1999

Polym. Adv. Technol.

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The syntheses of various deoxycelluloses and related structures (cellulosenes and anhydrocelluloses) from the mid‐1920s to the present are critically reviewed. General synthetic strategies to prepare deoxycelluloses include nucleophilic displacement of good leaving groups. Distinctions are made between reaction of cellulosics under homogeneous and heterogeneous conditions. Recent advances in the preparation of halodeoxycelluloses have led to high degree of substitution fluorodeoxycelluloses and bromodeoxycelluloses. Applications for the deoxycelluloses are numerous and characterized by biological, chemical or physical end uses.

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Section: Halodeoxycellulosessupporting

confidence: 60%

Deoxycelluloses and related structures

Vigo¹,

Sachinvala²

1999

Polym. Adv. Technol.

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“…Gas chromatographic and gas chromatographic-mass spectrometric analyses of the hydrolyzates of samples (as O-trifluoroacetyl derivatives) were carried out under the same conditions as described in the previous paper (11) . Silicone SE-30 (3% on Gas Chrom Q, 100-120 mesh) was used as a stationary phase.…”

Section: Analysesmentioning

confidence: 99%

“…Samples for analysis were hydrolyzed in sulfuric acid, and the hydrolyzates were converted into volatile 0-trifluoroacetyl derivatives for gas chromatographic and gas chromatographic-mass spectrometric analyses (11). Mass spectrometric analysis revealed that the peak material for each small peak was a dibromodideoxyaldohexose having one bromine atom at C-6.…”

Section: Chemical Structure Of Productsmentioning

confidence: 99%

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Bromination of Cellulose with Tribromoimidazole and Triphenylphosphine under Heterogeneous Conditions.

et al. 1994

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Bromination of bead cellulose was studied under heterogeneous conditions with tribromoimidazole and triphenylphosphine in several organic solvents. The addition of imidazole to the reaction system raised the degree of substitution with bromine (DSBr) of the products. The DSB, value increased at higher molar ratios of reagents to the repeating unit of cellulose and at longer reaction times, and exceeded 0.6 under appropriate conditions in dimethylacetamide or toluene-acetonitrile (1:2 v/v). The bromine distribution in the bromodeoxycellulose samples obtained was not homogeneous and 3,6-dibromo-3,6-dideoxyallose and 3,6-dibromo-3,6-dideoxyglucose units were contained even in the samples with DSB, lower than 0.5 along with 6-bromo-6-deoxyglucose and unmodified glucose units.

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“…were almost equal to those of KGM-Ts samples except that the absorption in the voa region became stronger relative to the pyranose absorptions in 1150-900 cm-1. In addition, a weak absorption was observed at 758cm-1 for samples with higher DSc, values ascribable to a C-Cl stretching vibration [9,26]. In the reactions in DMSO, the DSc, values attained were always smaller than those of the corresponding reactions in DMA.…”

Section: Effects Of Reaction Conditionsmentioning

confidence: 86%

Synthesis and Nucleophilic Substitution of Tosylated Konjac Glucomannan.

Takechi

Furuhata

1999

Sen-i Gakkaishi

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: Konjac glucomannan was treated with p-toluenesulfonyl (tosyl) chloride in an interfacial reaction.The tosylation proceeded effectively and the degree of tosylation (DST.) reached 2.34 under optimum conditions. Samples with DSTS values higher than about 0.5 were soluble in many kinds of organic solvents such as NN-dimethylacetamide (DMA), N,N-dimethylformamide, dimethyl sulfoxide, acetone, chloroform and pyridine while they were insoluble in water, methanol and ethanol. Tosylated samples were treated with lithium chloride, lithium bromide or sodium iodide in DMA. The NMR analysis of products showed that tosyloxy groups at C-6 were substituted with halogen atoms.

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Chlorination of cellulose with N-chlorosuccinimide-triphenylphosphine under homogeneous conditions in lithium chloride-N,N-dimethylacetamide

Cited by 39 publications

References 27 publications

Deoxycelluloses and related structures

Deoxycelluloses and related structures

Bromination of Cellulose with Tribromoimidazole and Triphenylphosphine under Heterogeneous Conditions.

Synthesis and Nucleophilic Substitution of Tosylated Konjac Glucomannan.

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