The sulfonyl analogue of phenoxathiin-based thiacalix[4]arene, easily accessible from the parent thiacalix[4]arene, reacts with sodium alkoxides to yield a cleaved product representing a novel type of macrocyclic skeleton with a quasi-calixarene structure. As shown by comparison with other derivatives, the internal strain imposed by the heterocyclic moiety is a driving force of this SNAr reaction.

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

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Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings

Reactivity of phenoxathiin-based thiacalixarenes towards C-nucleophiles