环丙烯酮与芳炔的反应：构建螺环呫吨-环丙烯结构单元
Reacting cyclopropenones with arynes: access to spirocyclic xanthene-cyclopropene motifs.
作者信息
Wallbaum Jan, Jones Peter G, Werz Daniel B
机构信息
†Technische Universität Braunschweig, Institut für Anorganische Chemie, Hagenring 30, 38106 Braunschweig, Germany.
出版信息
J Org Chem. 2015 Apr 3;80(7):3730-4. doi: 10.1021/acs.joc.5b00330. Epub 2015 Mar 19.
A formal insertion of two aryne moieties into the carbon-oxygen double bond of cyclopropenone has been realized. Spirocyclic xanthene-cyclopropene scaffolds were obtained. Mechanistically, a sequence of a formal [2 + 2]-cycloaddition followed by electrocyclic ring opening and a terminating [4 + 2]-type cycloaddition is postulated. The use of an electron-rich aryne precursor led to ring cleavage of the cyclopropene to afford an unprecedented xanthylium salt.
已实现将两个芳炔部分正式插入环丙烯酮的碳-氧双键中。得到了螺环呫吨-环丙烯支架。从机理上推测，首先是一个形式上的[2 + 2]环加成，接着是电环化开环，最后是一个终止的[4 + 2]型环加成。使用富电子芳炔前体导致环丙烯开环，得到了一种前所未有的呫吨鎓盐。
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