Thermodynamically Stable <i>o</i>‐Quinodimethane: Synthesis, Structure, and Reactivity
Kazuhiko Adachi, Shunsuke Hirose, Yasuyuki Ueda, Hidehiro Uekusa, Toshiyuki Hamura
Abstract
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.
Topics & Concepts
Steric effectsAryneIsomerizationChemistryRing (chemistry)Reactivity (psychology)CycloadditionStereochemistryMedicinal chemistryOrganic chemistryCatalysisAlternative medicinePathologyMedicineCyclization and Aryne ChemistrySynthesis and Properties of Aromatic CompoundsBioactive Compounds and Antitumor Agents