Synthesis of 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines and a demonstration of their reactivity to afford methano strap-modified Tröger's base analogues

Andrew B. Mahon, Donald C. Craig, Andrew C. Try

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)
    11 Downloads (Pure)

    Abstract

    Tröger's base analogues are of interest in areas such as host-guest chemistry, synthetic receptor design and asymmetric catalysis. We foresee that access to diverse functionality attached to the bridge of Tröger's base compounds will be beneficial for the development of these applications. As a starting point, we report a facile and general methodology to prepare a range of diversely functionalised 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines, compounds that may be viewed as "strap-clipped" Tröger's bases. As a demonstration of their reactivity, these compounds were reacted with benzaldehyde to introduce phenyl substituted straps onto a Tröger's base framework.

    Original languageEnglish
    Pages (from-to)148-163
    Number of pages16
    JournalArkivoc
    Volume2008
    Issue number12
    Publication statusPublished - 14 Apr 2008

    Bibliographical note

    Copyright the Publisher 2008. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

    Keywords

    • Tröger’s base
    • strap removal
    • diazocine
    • cyclic diam ines
    • trifluoroacetic anhydride
    • aldehyde condensation

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