Oxidative cyclodimerization after tandem cyclization of dehydrobenzo[14]annulenes induced by alkyllithium

Shunpei Nobusue*, Akihiro Shimizu, Kenji Hori, Ichiro Hisaki, Mikiji Miyata, Yoshito Tobe

*Corresponding author for this work

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

After eight: Reactions of dehydrobenzo[14]annulenes induced by the addition of n-butyllithium led to the discovery of an unprecedented oxidative cyclodimerization, which forms eight-membered ring products in up to 30 % yield. The product contains two indeno[2,1-a]fluorene components connected by a single and a double bond, which result from three transannular bond formations.

Original languageEnglish
Pages (from-to)4184-4188
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number15
DOIs
StatePublished - 8 Apr 2013

Keywords

  • annulenes
  • density functional calculations
  • dimerization
  • lithium
  • polycycles

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