Azatriquinanes. Part 4. The chemistry of azatriquinenamine and its bromination products

Manuel Lera, Alexander J. Blake, Claire Wilson, Mark Mascal

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Azatriquinenamine (5) is the entry point into the azatriquinane heterocycles. Its convex morphology and enamine function involving a bridgehead double bond lead to unusual reactivity. Bromination of 5 gives either a mono- (7) or tetrabromo (8) derivative depending on conditions, the latter of which is highly congested sterically and undergoes unexpected ring opening, rearrangement, and hydrolysis reactions. Careful elimination of HBr from 8 gives a potential precursor (14) to azatriquinene 6, and a dehydrobromination, bromination protocol leads to a potential precursor (18) to azatriquinacene 2.

Original languageEnglish (US)
Pages (from-to)3145-3149
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number23
StatePublished - 2001

ASJC Scopus subject areas

  • Chemistry(all)

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