New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads

Mughal EU, Kuck D (2010)
ORGANIC & BIOMOLECULAR CHEMISTRY 8(23): 5383-5389.

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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.
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Mughal EU, Kuck D. New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads. ORGANIC & BIOMOLECULAR CHEMISTRY. 2010;8(23):5383-5389.
Mughal, E. U., & Kuck, D. (2010). New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads. ORGANIC & BIOMOLECULAR CHEMISTRY, 8(23), 5383-5389.
Mughal, E. U., and Kuck, D. (2010). New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads. ORGANIC & BIOMOLECULAR CHEMISTRY 8, 5383-5389.
Mughal, E.U., & Kuck, D., 2010. New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads. ORGANIC & BIOMOLECULAR CHEMISTRY, 8(23), p 5383-5389.
E.U. Mughal and D. Kuck, “New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads”, ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 8, 2010, pp. 5383-5389.
Mughal, E.U., Kuck, D.: New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads. ORGANIC & BIOMOLECULAR CHEMISTRY. 8, 5383-5389 (2010).
Mughal, Ehsan U., and Kuck, Dietmar. “New C-3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads”. ORGANIC & BIOMOLECULAR CHEMISTRY 8.23 (2010): 5383-5389.
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