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Paper | Regular issue | Vol 92, No. 6, 2016, pp.1085-1094
Published online, 26th April, 2016
DOI: 10.3987/COM-16-13458
Selective Synthesis of Monosubstituted p-tert-Butylthiacalix[4]arene under Phase Transfer Catalysis

Omran A. Omran*

*Medical laboratory department, College of Science, Majmaah University, Zulfi, 1712, 11932, Saudi Arabia
Chemistry Department, Faculty of Science, Sohag University, Sohag, 82524, Egypt

Abstract

Phase transfer catalysis (PTC) technique for lower rim alkylation of p-tert-butylthiacalix[4]arene (TCA) with diethyl bromomalonate, phenacyl bromide, N,N-diethylchloroacetamide, ethyl bromoacetate and chloroacetonitrile using K2CO3, CsOH or Na2CO3 as a base and tetraethylammonium bromide (TEAB) as catalyst in benzene has been employed. Selective synthesis of monosubstituted p-tert-butylthiacalixarene using K2CO3 or CsOH as base has been elaborated. Unprecedented alkylation cyclization as well as arene oxidation by using of Na2CO3 as a base for alkylation of p-tert-butylthiacalix[4]arene under PTC conditions led to the synthesis of two new p-tert-butylthiacalix[4]arene derivatives with heterocyclic bridging rings. The structures of the newly synthesized compounds were characterized by different spectroscopy methods IR, 1H NMR, 13C NMR, and single crystal X-ray diffraction.