Functionalization of the methylene bridges of the calix[6]arene scaffold

The Journal of Organic Chemistry
Katerina KoganSilvio E Biali

Abstract

The bromine atoms of the hexabromo calixarene derivative 3 were replaced by other groups under S(N)1 conditions, allowing the facile synthesis of calix[6]arene derivatives incorporating identical functionalities at all bridges. Heating at reflux a mixture of 3 and the appropriate alcohol incorporated primary and secondary alkoxy substituents. Hydride abstraction was observed when the reaction with EtOH and i-PrOH was conducted in hexafluoroisopropanol (HFIP). Solvolysis of 3 in TFE in the presence of strong nucleophiles (such as N3(-) and aniline) afforded the corresponding hexaazido and hexaanilino derivatives. Hydroxyl groups were incorporated into the calix[6]arene scaffold via acetolysis of 3, followed by LiAlH4 reduction of the hexaacetate derivative obtained. Friedel-Crafts alkylations in the absence of Lewis acids were conducted by heating at reflux a mixture of 3, HFIP, and a substituted benzene derivative (e.g, m-xylene, p-methyl anisole, mesitylene). The calix[6]arene bridges were alkylated by heating at reflux a mixture of 3 and 2,4-pentanedione in TFE or HFIP. In all cases the reaction proceeded with high diastereoselectivity, and the major isomer isolated was assigned to the rc5 (i.e., all-cis) form. NMR spectrosco...Continue Reading

References

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Aug 17, 2002·The Journal of Organic Chemistry·Samah SimaanSilvio E Biali
Apr 26, 2003·The Journal of Organic Chemistry·Samah Simaan, Silvio E Biali
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Mar 12, 2005·Organic Letters·Eui-Hyun Ryu, Yan Zhao
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Mar 23, 2007·Organic Letters·Lev KunoSilvio E Biali
Apr 24, 2007·Organic Letters·Roberto SanzFélix Rodríguez
May 17, 2007·Organic Letters·Katerina Kogan, Silvio E Biali
Dec 7, 2007·The Journal of Organic Chemistry·Matthew ValeAndrzej Rajca
Mar 4, 2008·The Journal of Organic Chemistry·Ishay Columbus, Silvio E Biali

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Citations

Apr 13, 2011·The Journal of Organic Chemistry·Lev Kuno, Silvio E Biali
Jul 16, 2011·The Journal of Organic Chemistry·Sean P Bew, Sunil V Sharma
Aug 11, 2011·The Journal of Organic Chemistry·Katerina Kogan, Silvio E Biali
Feb 10, 2012·The Journal of Organic Chemistry·Ondrej KundratPavel Lhotak
Dec 25, 2013·The Journal of Organic Chemistry·David PomsSilvio E Biali
Nov 4, 2009·Chemical Communications : Chem Comm·Xiao-Hong TianChuan-Feng Chen
Aug 13, 2011·Chemical Communications : Chem Comm·Jean-Manuel RaimundoOlivier Siri
Jun 29, 2010·Chemistry : a European Journal·Xiao-Hong Tian, Chuan-Feng Chen
May 24, 2019·Chemistry : a European Journal·Ori Shalev, Silvio E Biali
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sergey N PodyachevAsiya R Mustafina
Dec 31, 2008·Organic Letters·Francesco TroisiPlacido Neri
Aug 27, 2009·The Journal of Organic Chemistry·Katerina Kogan, Silvio E Biali
Apr 28, 2010·The Journal of Organic Chemistry·Norbert Itzhak, Silvio E Biali

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