Xenon difluoride in the organic laboratory: a tale of substrates, solvents and vessels
Xenon difluoride in the organic laboratory: a tale of substrates, solvents and vessels
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有机实验室中的二氟化氙：底物、溶剂和容器的故事
DOI：
10.3998/ark.5550190.p008.436
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发表时间：
2013
期刊：
影响因子：
0.9
通讯作者：
C. Ramsden
中科院分区：
文献类型：
--
作者：
C. Ramsden
本报告总结了二氟化氙与有机底物反应的一系列研究。结果表明，二氟化氙与有机底物的反应有两种初始模式：单电子转移和亲电加成。讨论了芳基三甲基硅烷、羧酸和酯以及三甲基硅烯醇醚的反应。反应模式由溶剂、反应容器材料和酸催化剂的存在的组合决定。Pyrex，在烧瓶表面的形式，是一个非常有效的亲电反应的催化剂，但这种效果被抑制使用乙腈作为溶剂。三甲基甲硅烷基衍生物是特别方便的底物，因为它们避免了可能催化副反应的HF的形成。介绍了用[F]-XeF 2进行的一些研究。
This Account summarises a series of studies of the reactions of xenon difluoride with organic substrates. It is concluded that xenon difluoride has two initial modes of reaction with organic substrates: single electron transfer (SET) and electrophilic addition. Reactions of aryltrimethylsilanes, carboxylic acids and esters, and trimethylsilyl enol ethers are discussed. The mode of reaction is determined by a combination of the solvent, the reaction vessel material and the presence of an acid catalyst. Pyrex, in the form of a flask surface, is a very effective catalyst for electrophilic reactions but this effect is inhibited by use of acetonitrile as solvent. Trimethylsilyl derivatives are particularly convenient substrates as these avoid the formation of HF, which may catalyse side-reactions. Some studies using [F]-XeF2 are described.