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Gram‐Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9‐Tetramethyl[9](2,11)teropyrenophane
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-01-16 , DOI: 10.1002/anie.201713067
Kiran Sagar Unikela 1 , Tracey L. Roemmele 2 , Václav Houska 3 , Kaitlin E. McGrath 1 , David M. Tobin 2 , Louise N. Dawe 4 , René T. Boeré 2 , Graham J. Bodwell 1
Affiliation  

An improved synthetic pathway to the nanobelt‐like 1,1,9,9‐tetramethyl[9](2,11)teropyrenophane 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.

中文翻译:

1,1,9,9-四甲基[9](2,11)邻苯二甲醛的革兰氏合成和高区域选择性溴化

已经开发出了一种改进的合成途径,可以合成纳米带状的1,1,9,9-四甲基[9](2,11)萜品脱氧烷,并且可以合成克量的材料。关键的创新是依次进行氯化/ Friedel-Crafts烷基化反应,连续进行碘化/ Wurtz偶联反应和室温形成萜烯的反应。发现对苯二酚能够形成非常稳定的自由基阳离子,并进行完全区域选择性的四重溴化反应。
更新日期:2018-01-16
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