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Supramolecular Chemistry Volume 21, 2009 - Issue 7
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Original Articles

Regioselective alkylation of the lower rim of p-tert-butylthiacalix[4]arene with N-(p-nitrophenyl)-α-bromoacetamide

Ivan I. Stoikov A.M. Butlerov Chemical Institute, Kazan State University, Kazan, Russia
,
Dina S. Ibragimova A.M. Butlerov Chemical Institute, Kazan State University, Kazan, Russia
,
Nadezhda V. Shestakova A.M. Butlerov Chemical Institute, Kazan State University, Kazan, Russia
,
Dmitry B. Krivolapov A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan, Russia
,
Igor A. Litvinov A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan, Russia
,
Igor S. Antipin A.M. Butlerov Chemical Institute, Kazan State University, Kazan, Russia
,
Alexander I. Konovalov A.M. Butlerov Chemical Institute, Kazan State University, Kazan, Russia; A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan, Russia
&
Ilya Zharov Department of Chemistry, University of Utah, Salt Lake City, USACorrespondence[email protected]
 show all
Pages 564-571 | Received 30 Nov 2007, Accepted 14 Aug 2008, Published online: 22 Sep 2009
 
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Abstract

The preparation of partially substituted thiacalix[4]arenes 2–6 has been accomplished by conducting the reaction of the thiacalixarene 1 with N-(p-nitrophenyl)-α-bromoacetamide in acetone or acetonitrile in the presence of M2CO3 (M = Na, K and Cs). The influence of the reaction conditions (temperature, time, solvent, ratio of the reagents and the nature of the alkali metal carbonate) on regio- and stereoselectivity of this reaction is described.

Acknowledgements

The financial support from RFBR (06-03-32160), CRDF (RUC1-2825-KA-06), joint programme of CRDF and Ministry of Science and Education of RF ‘Fundamental researches and higher education’ (REC-007) is gratefully acknowledged.

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