THE ALKALINE REDUCTION OF AROMATIC NITRO COMPOUNDS WITH GLUCOSE
THE ALKALINE REDUCTION OF AROMATIC NITRO COMPOUNDS WITH GLUCOSE
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DOI：
10.1021/ja01147a138
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发表时间：
1951-01-01
影响因子：
15
通讯作者：
HITCH, EF
中科院分区：
文献类型：
--
作者：
GALBRAITH, HW;DEGERING, EF;HITCH, EF
本文研究了葡萄糖和碱还原芳香族硝基化合物为氧化偶氮化合物的条件，并建立了一套适用于多种硝基化合物的还原方法。22种化合物被成功地还原，转化率为40 - 100%。试验了15种在所用条件下不能还原的硝基化合物。在这一类中，邻硝基苯胺和对硝基苯胺及其取代产物是显著的，尽管间硝基苯胺还原平稳。葡萄糖分解形成的糖酸可能大部分是糖精型的，但还没有被确定。芳香族硝基化合物在碱性溶液中可以被葡萄糖还原的事实显然是由布劳恩在1865年首先发现的，他发现在加热含有苦味酸的碱性葡萄糖溶液时会显红色，他认为这是由于形成了苦味酸。从那时起，偶氮化合物的还原反应偶尔也被用于芳香族硝基化合物的还原，生成氧化偶氮化合物，偶氮化合物也有报道，偶氮化合物和羟胺化合物的分离也有报道。因此，Wacker 3能够将1-硝基萘-5-磺酸和1-硝基萘-3，5-二磺酸还原为相应的氧化偶氮化合物，并且将1-硝基蒽醌-2-磺酸还原为1-羟基氨基蒽醌-2-磺酸。4
The conditions affecting the reduction of aromatic nitro compoundsto azoxy compounds with glucose and alkali have been studied and a procedure evolved which has been applied to a variety of nitro compounds. Twenty-two compounds have been successfully reduced with conversions rangingfrom 40 to 100%. Fifteen nitro compounds were tested which could notbe reduced under the conditions employed. Conspicuous in this class are ortho-and para-nitroanilines and their substitution products, although the meta-nitroanilines reduce smoothly. The sugar acids formed by the breakdown of glucose are probably largely of the saccharinic type, but havenot been definitely identified.The fact that aromatic nitro compounds may be reduced by glucose in alkaline solution was apparently first discovered in 1865 by Braun, 2 who found that on heating an alkaline glucose solution with picric acid a red color developed, which he believed was due to the formation of picramic acid. Since that time the reaction has been occasionally employed in the reduction of aromatic nitro compoundsto yield azoxy com-pounds although azo compounds have been reported in a few cases and both the isolation of hydrazo and hydroxylamine compounds have been re-corded. Thus, Wacker3 was able to reduce 1-nitronaphthalene-5-sulfonic acid and 1-nitronaphthalene-3, 5-disulfonic acid to the corresponding azoxy compounds and l-nitroanthraquinone-2-sulfonic acidto l-hydroxylaminoanthraquinone-2-sulfonic acid. 4