Revisitation of cycloheptatriene derivatives as a building block for various substituted and fused 1,6-methano[10]annulenes and substituted 4,9-methanothia[11]annulenes

Shigeyasu Kuroda*, Takanori Kajioka, Atsushi Fukuta, Nguyen Chung Thanh, Yanmei Zhang, Ryuta Miyatake, Masaru Mouri, Shengli Zuo, Mitsunori Oda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A synthetic maneuver from 1,6-diacetyl- and 1,6-diformyl-1,3,5-cycloheptatrienes toward various 1,6-methano[10]annulenes, such as diaryl-substituted, cyclobutene-annulated, and thiophene-annulated derivatives and its quinodimethane-type compound, and 4,9-methanothia[11]annulenes is spotlighted based on our recent research efforts. The crystal structure analysis of the annulenes, discussion of mechanistic details of a key cyclization step and application of some annulene derivatives to a material in organic electroluminescent devices are also described.

Original languageEnglish
Pages (from-to)31-49
Number of pages19
JournalMini-Reviews in Organic Chemistry
Volume4
Issue number1
DOIs
StatePublished - 2007/02

Keywords

  • Cyclobutenes
  • Molecular orbital calculations
  • Organic electroluminescent device
  • Quinodimethanes
  • Thiophenes
  • X-ray crystallographic analysis

ASJC Scopus subject areas

  • Organic Chemistry

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