Abstract
6-Bromo-6-deoxycelluloses of a high degree of substitution were treated with various thiols under homogeneous conditions in lithium bromide/N,N-dimethylacetamide in the presence of triethylamine. At high temperatures, appreciable unfavorable side reaction, dehydrobromination yielding 3,6-anhydroglucose and/or 5,6-glucosene units took place. Under favorable conditions, more than 50% of bromine was substituted with thiols. Thiols used in this work include 2-hydroxyethanethiol, 2-aminoethanethiol, 4-aminobenzenethiol, 3-mercapto-propionic acid, 2-mercaptosuccinic acid, 2-mercaptobenzoic acid and cysteine. Solubilities of the products containing carboxyl, amino and/or hydroxyl groups were studied. Aminophenylthiodeoxycellulose was treated with nitrous acid followed by diazo coupling with N,N-dimethylaniline to yield a cellulosic dye.
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