Regioselective chlorination of chitin with N- chlorosuccinimide-triphenylphosphine under homogeneous conditions in lithium chloride-N,N-dimethylacetamide

Munenori Sakamoto, How Tseng, Ken ichi Furuhata

研究成果: 雜誌貢獻文章

21 引文 (Scopus)

摘要

Purified chitin was chlorinated with an equimolar mixture of N-chlorosuccinimide and triphenylphosphine under homogeneous conditions in a 5% (w/v) solution of LiCl in N, N- dimethylacetamide at 70-55°C. 13C NMR spectroscopy of the chlorinated products and gas chromatographic-mass spectrometric analysis of their hydrolyzates, both as trifluoroacetyl derivatives, showed that the chlorine substitution took place regioselectively at C-6. Chlorodeoxychitins with degrees of substitution up to 1.0 could be prepared easily by use of an excess of reagents. Polymer chain scission took place to some extent, especially when the chlorination was carried out at higher temperatures with higher concentrations of reagents.

原文英語
頁(從 - 到)271-280
頁數10
期刊Carbohydrate Research
265
發行號2
DOIs
出版狀態已發佈 - 十二月 16 1994
對外發佈Yes

指紋

Lithium Chloride
Chitin
Chlorination
Halogenation
Substitution reactions
Chlorine
Nuclear magnetic resonance spectroscopy
Polymers
Magnetic Resonance Spectroscopy
Gases
Derivatives
Temperature
dimethylacetamide
N-chlorosuccinimide
triphenylphosphine
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

引用此文

Regioselective chlorination of chitin with N- chlorosuccinimide-triphenylphosphine under homogeneous conditions in lithium chloride-N,N-dimethylacetamide. / Sakamoto, Munenori; Tseng, How; Furuhata, Ken ichi.

於: Carbohydrate Research, 卷 265, 編號 2, 16.12.1994, p. 271-280.

研究成果: 雜誌貢獻文章

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abstract = "Purified chitin was chlorinated with an equimolar mixture of N-chlorosuccinimide and triphenylphosphine under homogeneous conditions in a 5{\%} (w/v) solution of LiCl in N, N- dimethylacetamide at 70-55°C. 13C NMR spectroscopy of the chlorinated products and gas chromatographic-mass spectrometric analysis of their hydrolyzates, both as trifluoroacetyl derivatives, showed that the chlorine substitution took place regioselectively at C-6. Chlorodeoxychitins with degrees of substitution up to 1.0 could be prepared easily by use of an excess of reagents. Polymer chain scission took place to some extent, especially when the chlorination was carried out at higher temperatures with higher concentrations of reagents.",
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AU - Furuhata, Ken ichi

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N2 - Purified chitin was chlorinated with an equimolar mixture of N-chlorosuccinimide and triphenylphosphine under homogeneous conditions in a 5% (w/v) solution of LiCl in N, N- dimethylacetamide at 70-55°C. 13C NMR spectroscopy of the chlorinated products and gas chromatographic-mass spectrometric analysis of their hydrolyzates, both as trifluoroacetyl derivatives, showed that the chlorine substitution took place regioselectively at C-6. Chlorodeoxychitins with degrees of substitution up to 1.0 could be prepared easily by use of an excess of reagents. Polymer chain scission took place to some extent, especially when the chlorination was carried out at higher temperatures with higher concentrations of reagents.

AB - Purified chitin was chlorinated with an equimolar mixture of N-chlorosuccinimide and triphenylphosphine under homogeneous conditions in a 5% (w/v) solution of LiCl in N, N- dimethylacetamide at 70-55°C. 13C NMR spectroscopy of the chlorinated products and gas chromatographic-mass spectrometric analysis of their hydrolyzates, both as trifluoroacetyl derivatives, showed that the chlorine substitution took place regioselectively at C-6. Chlorodeoxychitins with degrees of substitution up to 1.0 could be prepared easily by use of an excess of reagents. Polymer chain scission took place to some extent, especially when the chlorination was carried out at higher temperatures with higher concentrations of reagents.

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