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

作者：Tsuchido Yoshitaka; Ide Tomohito; Suzaki Yuji; Osakada Kohtaro^*

来源：Bulletin of the Chemical Society of Japan, 2015, 88(6): 821-823.

DOI：10.1246/bcsj.20150017

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.

• 出版日期2015-6-15