Azatriquinanes: Synthesis, Structure, and Reactivity

Nicholas M. Hext, Jens Hansen, Alexander J. Blake, David E. Hibbs, Michael B. Hursthouse, Oleg V. Shishkin, Mark Mascal

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.

Original languageEnglish (US)
Pages (from-to)6016-6020
Number of pages5
JournalJournal of Organic Chemistry
Volume63
Issue number17
StatePublished - Aug 21 1998
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Hext, N. M., Hansen, J., Blake, A. J., Hibbs, D. E., Hursthouse, M. B., Shishkin, O. V., & Mascal, M. (1998). Azatriquinanes: Synthesis, Structure, and Reactivity. Journal of Organic Chemistry, 63(17), 6016-6020.