Poly-oxygenated tricyclobutabenzenes via repeated [2+2] cycloaddition of benzyne and ketene silyl acetal
Poly-oxygenated tricyclobutabenzenes via repeated [2+2] cycloaddition of benzyne and ketene silyl acetal
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DOI：
10.1021/ja0602647
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发表时间：
2006-03-22
影响因子：
15
通讯作者：
Suzuki, K
中科院分区：
文献类型：
--
作者：
Hamura, T;Ibusuki, Y;Suzuki, K
这里描述了一种高度官能化的三环丁苯的合成，三环丁苯是一类具有结构和理论意义的分子。该合成是基于苯乙炔和烯酮硅基缩醛(KSA)的重复[2+2]环加成反应，其中两种类型的区域选择性使得能够区分四元环上的官能团。通过这些步骤，我们能够制备多氧的八甲氧基三环丁苯及其水解型四氧代衍生物。对后者的结构研究表明，与应变四元环有关的有趣性质。
Described herein is a synthesis of highly functionalized tricyclobutabenzenes, a class of molecules of structural and theoretical interest. The preparation is based on the repeated [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where two types of regioselectivity enable discrimination of the functionalities on the four-membered rings. By these steps, we were able to prepare poly-oxygenated octamethoxytricyclobutabenzene and its hydrolyzed tetra-oxo derivatives. Structural study on the latter compound showed the interesting properties related to the strained four-membered ring.