PREPARATION OF 6-DEOXY-6-FLUOROCELLULOSE

PREPARATION OF 6-DEOXY-6-FLUOROCELLULOSE
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DOI:
10.1016/0008-6215(94)84043-1
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发表时间:
1994-07-16
影响因子:
3.1
通讯作者:
ISHIZU, A
ISHIZU, A
中科院分区:
化学3区
文献类型:
--
作者:
KASUYA, N;IIYAMA, K;ISHIZU, A

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以2,3-二乙酸纤维素(1)或2,3-二苯甲酸纤维素(2)为原料,在不同溶剂中制备了6-脱氧-6-氟纤维素,并通过F-19和C-13 NMR测量对其进行了表征。以硝基苯中2,3-二苯甲酸纤维素为原料制备的最佳产物在C-6和C-3的ds分别为0.95和0.04。起始材料和溶剂的其他组合在C-6上的氟ds较低(类似于0.8),在C-2或C-3上的氟ds较高(类似于0.12)。当使用1和1,4-二氧六环或2和氯仿的组合时,可以观察到C-2的取代。在C-2上被氟取代的产物相对耐酸水解。
6-Deoxy-6-fluorocellulose was prepared from cellulose 2,3-diacetate (1) or cellulose 2,3-dibenzoate (2) in various solvents, and was characterized by F-19 and C-13 NMR measurements. The best product, having ds of 0.95 at C-6 and 0.04 at C-3, was prepared from cellulose 2,3-dibenzoate in nitrobenzene. Other combinations of starting material and solvent gave a lower (similar to 0.8) ds of fluorine at C-6 and higher (similar to 0.12) at C-2 or C-3. Substitution at C-2 was observed when the combination of 1 and 1,4-dioxane, or 2 and chloroform was used. The products substituted at C-2 by fluorine were relatively resistant to acid hydrolysis.