HYDROXYLATION OF ANTHRAQUINONES IN OLEUM AND IN SULFURIC-ACID

被引:23
作者
BANKS, HJ [1 ]
CAMERON, DW [1 ]
RAVERTY, WD [1 ]
机构
[1] UNIV MELBOURNE,DEPT ORGAN CHEM,PARKVILLE 3052,VICTORIA,AUSTRALIA
关键词
D O I
10.1071/CH9782271
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The anthraquinone emodin (9) was rapidly and efficiently converted into catenarin (13) by treatment with a mixture of oleum and boric acid at room temperature. Chrysophanol (15) similarly gave islandicin (16), while related anthraquinones were hydroxylated in essentially the same way, though none as rapidly as emodin. The specificity of such processes is synthetically useful in generally involving substitution of the less highly hydroxylated ring. This is in contrast to hydroxylation with persulfate in sulfuric acid which, for emodin, occurred chiefly in the more highly hydroxylated ring, as did sulfonation. © 1978 Australian Journal of Chemistry.
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页码:2271 / 2282
页数:12
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