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Annulated oxa-cage frameworks via Claisen rearrangement and ring-closing metathesis
Tetrahedron ( IF 2.1 ) Pub Date : 2020-10-17 , DOI: 10.1016/j.tet.2020.131694
Sambasivarao Kotha , Subba Rao Cheekatla , Usha Nandan Chaurasia

In our quest to design high-density fuels, we report a variety of structurally interesting new annulated oxa-cage frameworks. Here, we investigated a linear synthetic sequence, which relies on reductive C–C bond cleavage and ring-closing metathesis as key steps. For this purpose, we utilized inexpensive and readily available starting materials such as hydroquinone and endo-dicyclopentadiene. Transannular cyclization during Grignard addition played a significant role in the design of intricate caged compounds. The creation of these new oxa-cage systems is a challenging task by traditional methods. The structure of the target compound has been unambiguously established by single-crystal X-ray diffraction studies. These data indicate that density of the RCM compound is larger than the cubane density.



中文翻译:

通过克莱森重排和闭环易位的环状氧笼框架

在设计高密度燃料的过程中,我们报告了各种结构有趣的新型环氧基氧-笼框架。在这里,我们研究了线性合成序列,该序列依赖于还原性C–C键断裂和闭环复分解为关键步骤。为了这个目的,我们使用了便宜且容易获得的原料,例如氢醌和内-二环戊二烯。在格利雅(Grignard)添加过程中,环过环化在复杂笼状化合物的设计中起着重要作用。通过传统方法,创建这些新的氧笼系统是一项艰巨的任务。通过单晶X射线衍射研究已经明确地确定了目标化合物的结构。这些数据表明,RCM化合物的密度大于古巴的密度。

更新日期:2020-11-12
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