1,3-dibromo-5,5-dimethylhydantoin
1,3-dibromo-5,5-dimethylhydantoin
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DOI：
10.1055/s-2005-872655
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发表时间：
2005-09-19
期刊：
影响因子：
2
通讯作者：
Alam, A
中科院分区：
文献类型：
--
作者：
Alam, A
溴代芳香族化合物是应用最广泛、研究最深入的溴代试剂之一。1由于溴化反应活性低、毒性大、操作不便，人们开发了一些替代溴化剂。然而，稳定的固体试剂总是优选的，特别是对于需要特定量的溴化试剂的小规模反应。另一方面，获得区域选择性单溴化也很重要，因为获得单溴化物和二溴化物的混合物是非常常见的。2市售的1，3-二溴-5，5-二甲基乙内酰脲（DBDMH）满足上述大部分要求。它是芳香环溴化的优良试剂，特别是酚和多酚。它提供了优异的产率与各种芳环，包括保护和未保护的苯酚和多酚衍生物，以及那些含有羧酸。反应通常较快，条件温和（室温或低于室温）。除了溴化活性，我们发现它是一个很好的氧化剂氧化硫醇的二硫化物在极高的产率。
Aromatic bromination with elemental bromine is one of the most widely used and extensively studied reagents. 1 Owing to low reactivity, high toxicity, and handling inconvenience, some alternative brominating agents have been developed. However, a stable, solid reagent is always preferred, particularly for small-scale reactions that require a specific amount of brominating reagent. On the other hand, getting regioselective monobromination is also important, because it is very common to obtain a mixture of monobromides and dibromides. 2 The commercially available 1, 3-dibromo-5, 5-dimethylhydantion (DBDMH) meets most of the requirements mentioned. It is an excellent reagent for the bromination of aromatic rings, particularly for phenols and polyphenols. It gives excellent yields with a variety of aromatic rings including protected and unprotected phenol and polyphenol derivatives, and those that contain carboxylic acids. The reaction is usually faster and the conditions are mild (at or below room temperature). In addition to the bromination activity, we found it to be an excellent oxidant for the oxidation of thiols to disulfides in extremely high yield.