Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene

Shigeyasu Kuroda*, Rie Kasai, Ryo Nagaya, Ryuta Miyatake, Yoshikazu Horino, Naoko Matsumoto, Mitsunori Oda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves π-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes.

Original languageEnglish
Pages (from-to)1426-1429
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number13
DOIs
StatePublished - 2011/03/30

Keywords

  • Cycloaddition
  • Electrocyclic reaction
  • Enamine
  • Methanothia-annulene
  • X-ray crystallographic analysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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