The von Auwers Reaction - History and Synthetic Applications
The von Auwers Reaction - History and Synthetic Applications
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DOI：
10.2533/chimia.2014.522
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发表时间：
2014-01-01
期刊：
影响因子：
1.2
通讯作者：
Jaeckh, Simon
中科院分区：
文献类型：
--
作者：
Dumeunier, Raphael;Jaeckh, Simon
从酚的容易的脱芳构化获得的二烯酮可以进一步转化为倾向于以干净但有时出乎意料的方式进行rearomatize的半苯。一百多年前，K。von Auwers发现在二烯酮上加入Grignards会自发地导致随后的脱水和新的芳构化重排。在梅尔文·纽曼重新调查这些发现之前，这种反应被忽视了50年，研究了机制，并在同一主题上发展了变化。从那时起，尽管反应的巨大潜力，这些研究很少被提及，最后被遗忘。这篇评论旨在为读者提供一个详细的历史和全面的参考书目的冯Auwers重排，它的一些合成应用，和新的未发表的材料，希望打开这个被遗忘的反应的新视角。
Dienones obtained from the facile dearomatization of phenols, can be further transformed to semi-benzenes prone to rearomatize in clean, but sometimes unexpected, fashion. Over a hundred years ago, K. von Auwers found that adding Grignards on dienones would lead spontaneously to subsequent dehydration and a novel aromatizing rearrangement. This reaction was ignored for 50 years before Melvin Newman re-investigated these findings, studied the mechanism, and developed variations on the same theme. Since then, despite the tremendous potential of the reactions, those studies were only rarely mentioned, before finally falling into oblivion. This review aims to provide the reader with a detailed history and comprehensive bibliography of the von Auwers rearrangement, some of its synthetic applications, and new unpublished material in the hope to open new perspectives on this forgotten reaction.