Study of Very Reactive Tautomeric Phenol Dienones as Dienes in Diels-Alder Reactions
Study of Very Reactive Tautomeric Phenol Dienones as Dienes in Diels-Alder Reactions
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DOI：
10.1021/ol8026768
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发表时间：
2009-03-19
期刊：
影响因子：
5.2
通讯作者：
Deslongchamps, Pierre
中科院分区：
文献类型：
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作者：
Dory, Yves L.;Roy, Andree-Lucie;Deslongchamps, Pierre
在Diels-Alder反应中，掩蔽的邻苯醌作为二烯伙伴是非常活泼的。仔细探索控制其令人惊讶的行为的轨道因素表明，它们的LUMO几乎与邻苯醌本身一样需要电子。在其二烯系统的任一端的甲基取代基通过改变反应途径或多或少地异步来影响活化能。
Masked ortho-benzoquinones are very reactive as diene partners in Diels-Alder reactions. Careful exploration of the orbital factors that govern their surprising behavior shows that their LUMO is almost as electron demanding as that of o-benzoquinone itself, Methyl substituents at either end of their diene system influence the activation energy through modification of the reaction pathway being more or less asynchronous.