THE STRUCTURE OF ANTHRAQUINONE-1-SULFENIC ACID (FRIES ACID) AND RELATED COMPOUNDS
THE STRUCTURE OF ANTHRAQUINONE-1-SULFENIC ACID (FRIES ACID) AND RELATED COMPOUNDS
复制标题
DOI：
10.1021/ja01522a066
复制
发表时间：
1959-01-01
影响因子：
15
通讯作者：
SAYIGH, AB
中科院分区：
文献类型：
--
作者：
BRUICE, TC;SAYIGH, AB
报道了甲基蒽醌-1-磺酸盐、二甲基蒽醌- 1,4 -二磺酸盐和甲基芴酮-1-磺酸盐羰基波段的定量红外光谱，并与蒽酮、蒽醌、芴酮以及1-羟基和1,4 -二羟基蒽醌进行了比较。得出的结论是，soch3基团与1-羟基、1-和2-氨基以及1-二甲基氨基一样，由于不对称导致醌吸收分裂。讨论了弗里斯酸（蒽醌-1-磺酸）及其衍生物的各种假设结构，并根据光谱证据对其进行了评价。结果表明，Fries的原始结构是正确的。当甲基蒽醌-1-磺酸甲酯(I)在规定条件下水解时，形成一种鲜红色的结晶化合物。根据实验式、制备方法、酸性质和甲醇处理后I的重组，Fries2将该物质的结构定为II，并注意到该产物在某些反应中的表现似乎与III处于平衡状态。在45年以来
Quantitative infrared spectra for the carbonyl bands of methyl anthraquinone-1-sulfenate, dimethyl anthraquinone-1, 4-disulfenate and methyl fluorenone-l-sulfenate are reported and compared to those for anthrone, anthraquinone, fluorenone and the 1-hydroxy-and 1, 4-dihydroxyanthraquinones. The conclusion is reached that the-SOCH3 group causes splitting of the quinone absorption, because of dissymmetry, just as does the 1-hydroxy, 1-and 2-amino and the 1-dimethyl amino groups. The various postulated structures for Fries’ acid (anthraquinone-1-sulfenic acid) as well as its derivatives are dis-cussed and evaluated in view of the spectroscopic evidence. It is concluded that the original structure of Fries is correct.When methyl anthraquinone-1-sulfenate (I) is hydrolyzed under prescribed conditions, a bright red, crystalline compound forms. On the basis of the empirical formula, means of preparation, acid nature and reformation of I on treatment with methanol, Fries2 assigned structure II to this sub-stance noting also that the product behaved in some of its reactions as though II were in equilibrium with III. In the forty-five years since the