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Reaction of 6-bromo-6-deoxycellulose with thiols in lithium bromide-N, N-dimethylacetamide

✍ Scribed by Nobuyoshi Aoki; Ken-Ichi Furuhata; Yasuo Saegusa; Shigeo Nakamura; Munenori Sakamoto

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 865 KB
Volume: 61
Category: Article
ISSN: 0021-8995
DOI: 10.1002/(sici)1097-4628(19960815)61:7<1173::aid-app13>3.0.co;2-z

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✦ Synopsis

Nucleophilic substitution reactions of 6-bromo-6-deoxycelluloses of high degrees of substitution with eight thiols having functional groups such as carboxyl and amino groups were studied under homogeneous conditions in LiBr-N,N-dimethylacetamide in the presence of triethylamine. The reactions under the homogeneous conditions proceeded more extensively than those run under heterogeneous conditions in aqueous alkaline solutions. The reactivity of thiols was found to increase with increasing acidity of the mercapto groups of the thiols. Reaction products with 2-mercaptobutanedioic acid and with 2-mercaptobenzoic acid were soluble in alkaline and neutral water but not in 1 N HCI, while the reaction products with 2-aminoethanethiol did not dissolve even in 1 N HCI. The reaction products with cysteine showed amphoteric behavior.

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