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

研究成果: Article査読

14 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)9116-9121
ページ数6
ジャーナルJournal of Organic Chemistry
76
21
DOI
出版ステータスPublished - 2011 11 4
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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