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

✍ Scribed by How Tseng; Ken-ichi Furuhata; Munenori Sakamoto

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 623 KB
Volume: 270
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00004-d

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✦ Synopsis

Chitin regenerated from LiCI-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.

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