Department of Organic Chemistry, University of Chemistry and Technology, Prague (UCTP), Technicka 5, 166 28 Prague 6, Czech Republic.
Org Biomol Chem. 2018 Jan 31;16(5):838-843. doi: 10.1039/c7ob03101g.
Regioselective meta-mercuration followed by Pd-catalysed intramolecular bridging gave birth to a novel type of calixarene bearing a single bond bridge between the meta positions of the neighboring aromatic subunits. These bridged derivatives possess extremely distorted cavities that imply possible amended properties over common calix[4]arenes. This new type of calixarene reactivity can be documented by acid-/electrophile-mediated cleavage of the basic macrocyclic skeleton leading to open oligomeric structures-the behavior of which has never been observed before in classic calix[4]arenes bearing alkoxy groups on the lower rim.
间位汞化反应再经钯催化的分子内桥接反应，生成了一种新型杯芳烃，其相邻芳环单元的间位通过单键桥连接。这些桥联衍生物具有极其扭曲的空腔，这意味着与常见的杯[4]芳烃相比，它们可能具有改良的性质。这种新型杯芳烃的反应性可以通过酸/亲电试剂介导的碱性大环骨架的断裂来证明，这导致了开环低聚物结构的形成——这种行为在以前经典的带有烷氧基的杯[4]芳烃中从未观察到过。
