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Structure–Property Relationships in Unsymmetric Bis(antiaromatics): Who Wins the Battle between Pentalene and Benzocyclobutadiene?

Péter J. Mayer, Ouissam El Bakouri, Tamás Holczbauer, Gergely F. Samu, Csaba Janáky, Henrik Ottosson, Gábor London

2020The Journal of Organic Chemistry32 citationsDOIOpen Access PDF

Abstract

]π subunits. We found that in the latter case the BCB unit alleviated its unfavorable antiaromaticity more efficiently, leaving the pentalene with strong antiaromaticity. Thus, a reversed structure-antiaromaticity relationship when compared to aceno-pentalenes was achieved.

Topics & Concepts

AntiaromaticityPentaleneAceneMoleculeChemistryRing (chemistry)Topology (electrical circuits)AromaticityStereochemistryCrystallographyOrganic chemistryMathematicsCombinatoricsSynthesis and Properties of Aromatic CompoundsAxial and Atropisomeric Chirality SynthesisPhotochromic and Fluorescence Chemistry