Abstract
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.
Original language | English |
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Pages (from-to) | 1774-1777 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 13 |
Issue number | 7 |
DOIs | |
Publication status | Published - 1 Apr 2011 |
Scopus Subject Areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry