Anthracene Capped Isobenzofuran: A Synthon for the Preparations of Iptycenes and Iptycene Quinones
详细信息 查看全文
- 作者：Bao-Jian Pei ; Wing-Hong Chan ; Albert W. M. Lee
- 刊名：Organic Letters
- 出版年：2011
- 出版时间：April 1, 2011
- 年：2011
- 卷：13
- 期：7
- 页码：1774-1777
- 全文大小：828K
- 年卷期：v.13,no.7(April 1, 2011)
- ISSN：1523-7052
文摘
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鈭扐lder 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.