Cover Image

The synthesis and alkylation of p-tetrakischloro-calix[4]arene

E. A. Ivanova, T. V. Glukhareva, Yu. Yu. Morzherin

Abstract


This work is devoted to the development of a chlorination of a calixarenes and a testing of the methods for their preparation to investigate the biological activity of the obtained compounds. New convinient undescribed in the literature methods of the chlorination using sulphuryl chloride or sodium hypochlorite were designed. By the using de-tert-butylcalix[4]arene, containing lower rin the ethoxy(hydroxy)carbonyl metoxy groups, as the starting compounds in the same reactin l aed to mixture of the produts. The reaction of the calix[4]arene and the sulfuryl chloride led to the tetra-kis-chlorocalix[4]arene with good yield (95 %).

Keywords


calixarene; chlorination; selectivity; alkylation

References


Kumar S, Chawla HM, Varadarajan R. A one-step, one-pot synthesis of p-acyl calix[n]arenes. Tetrahedron Lett. 2002;43(14):2495-98. doi:10.1016/S0040-4039(02)00325-8

Hapiot F, Lyskawa J, Bricout H, Tilloy S, Monflier E. Cyclodextrins or Calixarenes: What is the Best Mass Transfer Promoter for Suzuki Cross-Coupling Reactions in Water?. Adv Synth Catal. 2004;346(1):83-9. doi:10.1002/adsc.200303149

Gunji A, Takahashi K. Selective and Efficient Iodination of the p-Positions of Calix[4]arene Derivatives. Synth Commun. 1998;28(21):3933-41. doi:10.1080/00397919808004951

Carroll LT, Hill PA, Ngo CQ, Klatt KP, Fantini JL. Synthesis and reactions of a 2-chlorocalix[4]arene and a 2,2′-coupled dicalixarene. Tetrahedron. 2013;69:5002-7. doi:10.1016/j.tet.2013.04.010

Peles-Lemli B, Peles-Lemli J, Bitter I, Kollár L, Nagy G, Kunsági-Máté SJ. Competitive thermodynamic and kinetic processes during dissociation of some host-guest complexes of calix[4]arene derivatives. Incl Phen Macrocycl Chem. 2007;59:251-6. doi:10.1007/s10847-007-9322-3




DOI: https://doi.org/10.15826/chimtech.2014.1.1.729

Copyright (c) 2014 E. A. Ivanova, T. V. Glukhareva, Yu. Yu. Morzherin

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Scopus logo WorldCat logo DOAJ logo CAS logo BASE logo eLibrary logo

© Website Chimica Techno Acta, 2014–2024
ISSN 2411-1414 (Online)
This journal is licensed under a Creative Commons Attribution 4.0 International