[4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone
[4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone
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DOI：
10.1002/chem.201504013
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发表时间：
2016-01-11
影响因子：
4.3
通讯作者：
Werz, Daniel B.
中科院分区：
文献类型：
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作者：
Garve, Lennart K. B.;Pawliczek, Martin;Werz, Daniel B.
两亲性苯并二硫杂环亚胺与给受体环丙烷反应，合成了含两个硫原子的七元杂环。形式上，这种转化可以被认为是三元环和邻二硫代醌的[4+3]环加成反应。苯并二硫杂环亚胺用作这种高反应性二烯的替代物。产物的结构经X-射线晶体学确证。在C-13 NMR研究中的宽信号表明，在室温下存在几种构象异构体，在NMR时间尺度上缓慢地相互转化。
Donor-acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven-membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a [4+3] cycloaddition reaction of the three-membered ring and ortho-bisthioquinone. The benzodithioloimine serves as a surrogate for this highly reactive diene. The structure of the products was confirmed by X-ray crystallography. Broad signals in C-13 NMR studies suggest that several conformers, slowly interconverting on the NMR timescale, are present at room temperature.