1,4-Selective Diels-Alder Reaction of 9,10-Diethynylanthracene with 3,6-Difluorobenzyne

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<jats:title>Abstract</jats:title> <jats:p>Diels–Alder reaction of 9,10-bis(3-hydroxy-3-methyl-1-butynyl)anthracene with 3,6-difluorobenzyne yields the naphthobarrelene derivative via 1,4-addition of difluorobenzyne in a higher yield than the 9,10-adduct having a triptycene core. The DFT calculations revealed that the intermediate for the former reaction is stabilized more significantly by attractive interaction between a fluorine atom at the benzyne ring and a hydrogen atom at the anthracene ring.</jats:p>

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