Russian Chemical Reviews ( IF 7.0 ) Pub Date : 2021-03-30 , DOI: 10.1070/rcr4971 Vitaly Aleksandrovich Osyanin , Anton Vladimirovich Lukashenko , Dmitry Vladimirovich Osipov
The review summarizes and systematizes the [4+2]-cycloaddition reactions of o-quinone methides with electron-rich and electron-deficient olefins. The electron-rich substrates include vinyl ethers, vinyl sulfides, enamines, enamides, enols, furans, benzofurans and indoles, while the electron-deficient substrates are esters of unsaturated carboxylic acids, vinyl azides and quinones. Reactions with push-pull and captodative olefins are also considered. The mechanisms of some reactions are presented. A separate part of the review addresses reactions of p-quinone methides containing an o-hydroxyphenyl substituent at the exocyclic carbon atom, which can isomerize to o-quinone methides. Much attention is paid to oligomerization of o-quinone methides, which proceeds in the absence of active dienophiles or nucleophiles.
The bibliography includes 217 references.
中文翻译:
邻醌甲基化物与极化烯烃的环加成反应
该综述总结并系统化了邻醌甲基化物与富电子和缺电子烯烃的[4+2]-环加成反应。富电子底物包括乙烯基醚、乙烯基硫化物、烯胺、烯酰胺、烯醇、呋喃、苯并呋喃和吲哚,而缺电子底物是不饱和羧酸酯、乙烯基叠氮化物和醌。还考虑了与推拉和俘获烯烃的反应。介绍了一些反应的机理。评论的一个单独部分讨论了在环外碳原子上含有邻羟基苯基取代基的对醌甲基化物的反应,该取代基可以异构化为邻醌甲基化物。高度重视低聚化o-醌甲基化物,在没有活性亲二烯体或亲核体的情况下进行。
参考书目包括 217 篇参考文献。