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New C(3v)-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads.
MedLine Citation:
PMID:  20877782     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
A series of tribenzotriquinacene derivatives bearing three oxy-functionalised alkyl groups at the benzhydrylic bridgeheads (C-4b, C-8b and C-12b) have been synthesised. The 4b,8b,12b-triallyl derivative was used to generate the corresponding TBTQ-tris-acetaldehyde and TBTQ-tris(acetic acid), in which the functional groups stretch out from the convex rigid molecular surface. The corresponding tribromo derivate was found to undergo smooth Lewis acid-catalyzed C-C coupling with appropriate silyl enol ethers to afford a series of threefold 4b,8b,12b-(2-oxoalkyl)-substituted tribenzotriquinacenes. Six-fold nitration at the arene periphery was performed with 4b,8b,12b-tripropyltribenzotriquinacene and with the TBTQ-tris(acetic acid) to check for the effect of the bridgehead groupings as solubilising auxiliaries.
Authors:
Ehsan U Mughal; Dietmar Kuck
Publication Detail:
Type:  Journal Article     Date:  2010-09-27
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  8     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2010 Dec 
Date Detail:
Created Date:  2010-11-10     Completed Date:  2011-02-01     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  5383-9     Citation Subset:  -    
Affiliation:
Department of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany.
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