Electrophilic transannular cyclization of octadehydrodibenzo[12]annulene reexamined: Indication of the formation of both anti-and syn-indenofluorenes

Takashi Takeda, Koji Inukai, Kazukuni Tahara, Yoshito Tobe

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The reaction of tetrabutoxyoctadehydrodibenzo[12]annulene 2f with iodine under aerobic conditions was reexamined. Contrary to previous reports, the present results revealed the formation of both anti-diiodoindenofluorenedione and its syn isomer through the oxidation of the respective tetraiodoindenofluorenes, indicating the occurrence of two modes of iodine-induced transannular cyclization. This was supported by the reaction of 2f with bromine, which gave anti- and syn-hexabromodihydroindenofluorenes through interception of indenofluorene intermediates by bromine. The hexabromides were transformed into the corresponding dibromodiones by hydrolysis.

Original languageEnglish
Pages (from-to)9116-9121
Number of pages6
JournalJournal of Organic Chemistry
Volume76
Issue number21
DOIs
Publication statusPublished - 2011 Nov 4
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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