Thermodynamically Stable  o ‐Quinodimethane: Synthesis, Structure, and Reactivity | Zendy

Adachi Kazuhiko | Zendy; Hirose Shunsuke | Zendy; Ueda Yasuyuki | Zendy; Uekusa Hidehiro | Zendy; Hamura Toshiyuki | Zendy

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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.

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