Azatriquinane, azatriquinacene, and a remarkable dimerization product

Mark Mascal, Nicholas M. Hext, Oleg V. Shishkin

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

Azatriquinane, an amine with a rigid, hemispherical topology, is synthesized in six steps from pyrrole. It is shown to be more basic than quinuclidine, and can be dimerized by N-oxidation and treatment with base to give novel, highly strained heptacycle. Oxidation with chlorine gives an azatriquinacene, a theoretical precursor to diazadodecahedrane.

Original languageEnglish (US)
Pages (from-to)131-134
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number1
DOIs
StatePublished - Jan 1 1996
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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