Zhang Yang, Tong Shuo, Wang Mei-Xiang
MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Angew Chem Int Ed Engl. 2020 Oct 5;59(41):18151-18155. doi: 10.1002/anie.202006231. Epub 2020 Aug 11.
Described in this paper are the synthesis and structure of novel and edge-functionalized zigzag hydrocarbon belts. A stepwise "fjord-stitching" strategy featuring repetitive intramolecular acylation reactions of a resorcin[4]arene derivative as the key steps afforded a biscarbonyl-functionalized octahydrobelt[8]arene product. Facile ketone reduction with NaBH and nucleophilic addition with n-butyllithium produced secondary and tertiary alcohol-containing molecular belts, respectively. Selective oxidation reactions of biscarbonyl-bearing octahydrobelt[8]arene with m-CPBA and (PhSeO) O furnished the corresponding lactone- and 1,4-quinone-embedded molecular belts. Depending on the functional groups on the edges, the acquired belt molecules adopt different shapes such as square prism, truncated cone, and elliptical cylinder.
本文描述了新型边缘功能化锯齿状碳氢化合物带的合成与结构。一种逐步的“峡湾缝合”策略，其关键步骤是间苯二酚[4]芳烃衍生物的重复分子内酰化反应，得到了双羰基功能化八氢带[8]芳烃产物。用硼氢化钠轻松还原酮以及用正丁基锂进行亲核加成，分别生成了含仲醇和叔醇的分子带。含双羰基的八氢带[8]芳烃与间氯过氧苯甲酸（m-CPBA）和二苯基二硒醚（(PhSeO)₂O）的选择性氧化反应，提供了相应的内酯和嵌入1,4-醌的分子带。根据边缘上的官能团不同，所获得的带分子呈现出不同的形状，如方柱体、截顶圆锥体和椭圆柱体。
