TY - JOUR
T1 - Bromination of regenerated chitin with N-bromosuccinimide and triphenylphosphine under homogeneous conditions in lithium bromide-N,N-dimethylacetamide
AU - Tseng, How
AU - Furuhata, Ken ichi
AU - Sakamoto, Munenori
PY - 1995/4/30
Y1 - 1995/4/30
N2 - 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.
AB - 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.
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U2 - 10.1016/0008-6215(95)00004-D
DO - 10.1016/0008-6215(95)00004-D
M3 - Article
AN - SCOPUS:0029064413
SN - 0008-6215
VL - 270
SP - 149
EP - 161
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 2
ER -