Dispiro[cyclohexane-1,1′-(1′,7′- dihydrocyclopenta[f]azulenium)-7′,1′′-cyclohexane] perchlorate, a new highly stable hydrocarbon cation

Mitsunori Oda*, Hitoshi Kainuma, Ryuta Miyatake, Shigeyasu Kuroda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The title cation was synthesized from 1,6-diacetylcyclohepta-1,3,5-triene by a six-step sequence involving an aldol reaction, the Nazarov cyclization, the Shapiro reaction and hydride abstraction, and its pKR+ value was found to be 13.2, providing a new access to highly stable hydrocarbon cations.

Original languageEnglish
Pages (from-to)3485-3488
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number19
DOIs
StatePublished - 2002/05/06

Keywords

  • Azulenes
  • Carbenium ions
  • Cyclohexanes
  • Spiro compounds
  • X-ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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