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Thermodynamically Stable o ‐Quinodimethane: Synthesis, Structure, and Reactivity
Author(s) -
Adachi Kazuhiko,
Hirose Shunsuke,
Ueda Yasuyuki,
Uekusa Hidehiro,
Hamura Toshiyuki
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004510
Subject(s) - steric effects , aryne , isomerization , chemistry , ring (chemistry) , reactivity (psychology) , cycloaddition , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.