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

页码：3665 / 3669

页数：5

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