2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate

Kiyoshi Matsumoto*, Sadahito Goto, Naoto Hayashi, Hirokazu Iida, Takane Uchida, Akikazu Kakehi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A 3-azabicyclo[3.2.0]hepta-1,4-diene with no substituent in the cyclobutene moiety has been prepared for the first time; it undergoes extremely facile electrophilic attack at the β-position to give the ring-opened product, probably by a retro-Friedel-Crafts process. The title compound also undergoes a novel reaction with dimethyl acetylenedicarboxylate to afford the azepine.

Original languageEnglish
Pages (from-to)4667-4671
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number22
DOIs
StatePublished - 2004/11/12

Keywords

  • Azepine
  • Retro-Friedel - Crafts reaction
  • Ring opening
  • Small ring system

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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