Thermodynamically Stable o-Quinodimethane: Synthesis, Structure, and Reactivity

被引：6
|
作者：
Adachi, Kazuhiko [1 ]
Hirose, Shunsuke [1 ]
Ueda, Yasuyuki [1 ]
Uekusa, Hidehiro [2 ]
Hamura, Toshiyuki [1 ]
机构：
[1] Kwansei Gakuin Univ, Dept Appl Chem Environm, 2-1 Gakuen, Sanda 6691337, Japan
[2] Tokyo Inst Technol, Sch Sci, Dept Chem, Meguro Ku, Ookayama 2, Tokyo 1528551, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 11期
关键词：
aryne; cycloaddition; cyclobutaarenes; polycyclic aromatic hydrocarbon; quinodimethanes; CONROTATORY ELECTROCYCLIC REACTIONS; CARBON-CARBON; RING OPENINGS; PRECURSOR; ARYNE; 7,7,8,8-TETRAARYL-O-QUINODIMETHANE; STEREOSELECTIVITIES; CYCLOBUTENES; BENZYNE; SYSTEM;
D O I：
10.1002/chem.202004510
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Thermal isomerization of cyclobutaphenanthrene to o-quinodimethane was investigated. Sterically congested substituents or electron-donating substituents on the four-membered ring promoted the ring-opening, affording o-quinodimethane in a relatively stable form. Isolation of the newly prepared o-quinodimethane allowed its structural elucidation and investigation of its potential reactivities. Dual [4+2] cycloaddition of an aryne and o-quinodimethane afforded tetrabenzopentacene, demonstrating the synthetic application of the isolated compound.
引用
收藏
页码：3665 / 3669
页数：5
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