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

Bao Jian Pei, Wing Hong CHAN, Albert W M LEE

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

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 languageEnglish
Pages (from-to)1774-1777
Number of pages4
JournalOrganic Letters
Volume13
Issue number7
DOIs
Publication statusPublished - 1 Apr 2011

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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