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Syntheses of Novel Hexahomotrithiacalix[3]arenes

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Abstract

The first synthesis of the C 3 -symmetrical p-tert-butylhexahomotrithiacalix[3]arene 7d via one-pot procedure by the reaction of 2,6-bis(chloromethyl)-p-tert-butylphenol 8d with sodium sulfide nanohydrate under high-dilution conditions is reported. Also, hexahomotrithiacalix[3]arenes 7d-f (where d-f designate the type of the substituents R at the p-positions of the phenolic rings: d, R=t-Bu; e, R=CH3; f, R=Cl) were synthesized via a convergent approach in good yield by the [2+1] cyclization reaction of 2,6-bis(chloromethyl)phenol monomers 8d-f and bis(chloromethyl)phenol dimers 15d-f in presence of sodium sulfide nanohydrate under high-dilution conditions. The structures of 7d-f were determined by 1H, 13C NMR, MS and elemental analysis. A preliminary study of the binding properties of 7d with alkali- and heavy metal cations using biphasic picrate extraction method showed only weak abilities to bind the cations examined.

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  1. Chemistry Department, Mutah University, Mutah, Al-Karak, Jordan

    Muhammad Ashram

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  1. Muhammad Ashram
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Correspondence to Muhammad Ashram.

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Ashram, M. Syntheses of Novel Hexahomotrithiacalix[3]arenes. J Incl Phenom Macrocycl Chem 54, 253–259 (2006). https://doi.org/10.1007/s10847-005-8648-y

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  • DOI: https://doi.org/10.1007/s10847-005-8648-y

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