Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones

Language

English

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. © 2011 American Chemical Society.

Publication Date

2011

Source Publication Title

Organic Letters

Volume

13

Issue

7

Start Page

1774

End Page

1777

Publisher

American Chemical Society

DOI

10.1021/ol200309v

Link to Publisher's Edition

http://dx.doi.org/10.1021/ol200309v

ISSN (print)

15237060

ISSN (electronic)

15237052

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