Electrophilic tandem transannular cyclization of octadehydrotribenzo[14]annulene to benzodiindenocyclooctatetraenes

Shunpei Nobusue, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Treatment of octadehydrotribenzo[14]annulene ([14]DBA) with bromine or iodine gave the corresponding tetrahalosubstituted benzodiindenocyclooctatetraenes selectively via tandem twofold transannular bond formations. The exclusive mode of cyclization in contrast to that observed for the nucleophile-induced cyclizations is interpreted in terms of the relative stabilities of the key intermediates in both processes.

Original languageEnglish
Pages (from-to)1210-1212
Number of pages3
JournalChemistry Letters
Volume43
Issue number8
DOIs
StatePublished - 1 Jan 2014

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