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克级规模合成及 1,1,9,9-四甲基[9](2,11)并苝二萘嵌苯的高区域选择性溴化

Gram-Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9-Tetramethyl[9](2,11)teropyrenophane.

机构信息

Department of Chemistry, Memorial University of Newfoundland, St. John's, NL, A1B 3X7, Canada.

Department of Chemistry, University of Lethbridge, 4401 University Drive, Lethbridge, AB, T1K 3M4, Canada.

出版信息

Angew Chem Int Ed Engl. 2018 Feb 5;57(6):1707-1711. doi: 10.1002/anie.201713067. Epub 2018 Jan 16.

Abstract

An improved synthetic pathway to the nanobelt-like 1,1,9,9-tetramethyl9teropyrenophane has been developed, and enables the synthesis of gram quantities of material. Key innovations are the development of a sequential chlorination/Friedel-Crafts alkylation reaction, a sequential iodination/Wurtz coupling reaction, and a room-temperature teropyrene-forming reaction. The teropyrenophane was found to form a very stable radical cation and undergo a completely regioselective fourfold bromination reaction.

摘要

已经开发出一种改进的纳米带状 1,1,9,9-四甲基9苝并菲烷的合成途径,并且能够合成克数量级的材料。关键的创新是开发了一个顺序氯化/Friedel-Crafts 烷基化反应、一个顺序碘化/Wurtz 偶联反应和一个室温苝形成反应。发现苝并菲烷形成非常稳定的自由基阳离子,并经历完全区域选择性的四步溴化反应。

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