Bromination of regenerated chitin with N-bromosuccinimide and triphenylphosphine under homogeneous conditions in lithium bromide-N,N-dimethylacetamide

How Tseng, Ken ichi Furuhata, Munenori Sakamoto

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Chitin regenerated from LiCl-N,N-dimethylacetamide (DMA) was found to dissolve in 10 g/dL LiBr-DMA. The bromination of the regenerated chitin proceeded to a large extent (DS by bromine up to 0.94) with equimolar amounts of N-bromosuccinimide and triphenylphosphine under homogeneous conditions in LiBr-DMA at 50-90°C. 13C NMR spectroscopy of brominated products and GLC-MS analysis of their hydrolyzates showed that the bromine substitution took place regioselectively at C-6 of the chitin repeating units. Polymer chain scission occurred to some extent during the bromination, more extensively at higher temperatures with higher concentrations of reagents.

Original languageEnglish
Pages (from-to)149-161
Number of pages13
JournalCarbohydrate Research
Volume270
Issue number2
DOIs
Publication statusPublished - Apr 30 1995
Externally publishedYes

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Bromosuccinimide
Chitin
Halogenation
Bromine
Nuclear magnetic resonance spectroscopy
Polymers
Substitution reactions
Magnetic Resonance Spectroscopy
Temperature
dimethylacetamide
triphenylphosphine
lithium bromide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Bromination of regenerated chitin with N-bromosuccinimide and triphenylphosphine under homogeneous conditions in lithium bromide-N,N-dimethylacetamide. / Tseng, How; Furuhata, Ken ichi; Sakamoto, Munenori.

In: Carbohydrate Research, Vol. 270, No. 2, 30.04.1995, p. 149-161.

Research output: Contribution to journalArticle

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