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Chemoselective Oxidation of Phenoxathiin-Based Thiacalix[4]arene and the Stereoselective Alkylation of Products

Abstract

Phenoxathiin-based thiacalix[4]arene, accessible via acid-catalysed rearrangement of the starting spirodienone derivative, was subjected to the oxidation of sulfur bridging groups. Using the excess of the oxidation agent, systems bearing four sulfonyl groups or three sulfonyl and one sulfoxide group are available in high yields, depending on the reaction conditions. Although four different conformations can be obtained, the alkylation with various alkylating agents led stereoselectively to derivatives being immobilized in the partial cone conformation. The structure of products was assigned using the combination of NMR techniques and single crystal X-ray analysis. All compounds represent inherently chiral building blocks potentially useful in the design of novel thiacalixarene-based receptors.

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Publication details

The article was received on 14 Sep 2018, accepted on 06 Nov 2018 and first published on 07 Nov 2018


Article type: Paper
DOI: 10.1039/C8NJ04690E
Citation: New J. Chem., 2018, Accepted Manuscript
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    Chemoselective Oxidation of Phenoxathiin-Based Thiacalix[4]arene and the Stereoselective Alkylation of Products

    T. Landovsky, H. Dvorakova, V. Eigner, M. Babor, M. Krupicka, M. Kohout and P. Lhotak, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ04690E

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