Department of Chemistry
Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones
Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl) isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)2/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized. © 2011 American Chemical Society.
Source Publication Title
American Chemical Society
Link to Publisher's Edition
Pei, Bao-Jian, Wing-Hong Chan, and Albert W. M. Lee. "Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones." Organic Letters 13.7 (2011): 1774-1777.