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

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

Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.14/84772

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Title: Synthesis of 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines and a demonstration of their reactivity to afford strap-modified Tröger's base analogues
Related: ARKIVOC, Vol. 2008, Pt. xii, p.148-163
Related: http://www.arkat-usa.org/get-file/23477
Related: http://www.arkat-usa.org/get-file/23475
Publisher: ARKAT USA
Date: 2008
FoR/RFCD Code(s): 030500 Organic Chemistry
Author/Creator: Mahon, Andrew B
Author/Creator: Craig, Donald C
Author/Creator: Try, Andrew C
Description: 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.
Description: 16 page(s)
Subject Keyword: 030500 Organic Chemistry
Subject Keyword: Tröger’s base
Subject Keyword: strap removal
Subject Keyword: diazocine
Subject Keyword: cyclic diamines
Subject Keyword: trifluoroacetic anhydride
Subject Keyword: aldehyde condensation
Resource Type: journal article
Organisation: Macquarie University. Dept. of Chemistry and Biomolecular Sciences

Identifier: http://hdl.handle.net/1959.14/84772
Identifier: ISSN:1551-7012
Identifier: mq-rm-2007010694
Language: eng
Rights: 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.
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