Azatriquinane, azatriquinacene, and a remarkable dimerization product

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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

Fingerprint

Quinuclidines
Pyrroles
Dimerization
Chlorine
Amines
Oxidation
Topology

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Azatriquinane, azatriquinacene, and a remarkable dimerization product. / Mascal, Mark; Hext, Nicholas M.; Shishkin, Oleg V.

In: Tetrahedron Letters, Vol. 37, No. 1, 01.01.1996, p. 131-134.

Research output: Contribution to journalArticle

Mascal, Mark ; Hext, Nicholas M. ; Shishkin, Oleg V. / Azatriquinane, azatriquinacene, and a remarkable dimerization product. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 1. pp. 131-134.
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