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

Munenori Sakamoto, How Tseng, Ken ichi Furuhata

Research output: Contribution to journalArticle

21 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)271-280
Number of pages10
JournalCarbohydrate Research
Volume265
Issue number2
DOIs
Publication statusPublished - Dec 16 1994
Externally publishedYes

Fingerprint

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

Keywords

  • Chitin, regioselective chlorination of
  • Polysaccharide, homogeneous chlorination
  • Regioselective chlorination of chitin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

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

In: Carbohydrate Research, Vol. 265, No. 2, 16.12.1994, p. 271-280.

Research output: Contribution to journalArticle

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