Abstract
A new bridging reagent,N,N′-bis (chloroacetyl) propylenediamine was used to explore the relative activity and bridging pattern ofp-tert-butylcalix[4] arene,p-tert-butylcalix[6] arene and butylcalix[8] arene. It was found that the bridging reaction is selectively, at least, preferably at 1,3-position forp-tert-butylcalix [4] arene andp-tert-butylcalix[6]arene, 1,5-position forp-tert-butylcalix [8]arene. Taking the yield of bridged calixarene as a comparsion standard, the activity decreases with the increasing of the number of phenolic units in calixarene.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Gutsche C D.Calixarenes Revised. Cambridge: the Royal Society of Chemistry, 1998.
Asfari Z, Böhmer V, Harrowfield J,et al. Calixarene. 2001. Dordrecht: Kluwer Academic Publishers, 2001. 63–88.
Neri P, Consoli G M L, Cunsolo F,et al. Chemistry of Larger Calix[n]arenes (n=7,8,9), In: Asfari Z, Böhmer V, Harrowfield J,et al eds.Calixarene 2001. Dordrecht: Kluwer Academic Publishers, 2001. 89–109.
Pochini A, Ungaro R.Calixarenes and Related Hosts. In: Lehn J M, Vögtle F eds.Comprehensive Supramolecules Chemistry. Oxford: Elsevier Science, 1996. 2, 103–142.
Chen Y Y, Gong S L. Bridged Calix[6]arenes.J Inclusion Phenom, 2003,45:165–184.
Gutshe C D, Iqbal M.p-tert-Butylcalix[4] arene.Org Synth, 1990,68:234–236.
Gutshe C D, Iqbal M.p-tert-Butylcalix [6] arene,Org Synth, 1990,68:237–240.
Gutshe C D, Iqbal M.p-tert-Butylcalix[8] arene,Org Synth, 1990,68:241–243.
Philp C H United States.Herbicides, Patent US, 2864684, Dec 9, 1958.
Geraci C, Piattelli M, Chessari G,et al. Singly Bridged Calix[8]crowns.J Org Chem, 2000,65:5143–5151.
Geraci C, Piattelli M, Neri P. Regioselective Synthesis of Calix[8]crowns by Direct Alkylation ofp-tert-Butylcalix[8] arene.Tetrahedron Lett, 1996,37:3899–3902.
Cunsolo F, Consoli G M I, Piattelli M,et al. Methylation ofp-tert-Butylcalix[8]arene. Products Obtained in the Presence of Strong Bases.J Org Chem, 1998,64:6852–6858.
Li J S, Chen Y Y, Lu X R. Selective Bridging ofp-tert-Butylcalix [6]arene with Polyethylene Glycol Ditosylates,Tetrahedron, 1999,55:10635–10374.
Chen Y Y, Li J S, **n J,et al. Syntheses of Lower-Rim-1, 3-Crowned Calix[6]arenes and Their Complexation.Synth Commun, 1999,29:705–712.
Chen Y Y, Yang F F, Gong S L. Molecular Design and Synthesis of a Calix[6]crown-Based Lithium-Selective Ionophore.Tetrahedron Lett, 2000,41:4815–4818.
Author information
Authors and Affiliations
Corresponding author
Additional information
Foundation item: Supported by the National Natural Science Foundation of China (20272044).
Biography: LI Jun (1978-), female, Master candidate, research direction: calixarene chemistry
Rights and permissions
About this article
Cite this article
Jun, L., Wei, W., Shu-ling, G. et al. Bridging of calixarenes withN,N′-bis (chloroacetyl) propylenediamine. Wuhan Univ. J. Nat. Sci. 9, 509–512 (2004). https://doi.org/10.1007/BF02830453
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02830453