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      Regioselective SNAr reaction of the phenoxathiin-based thiacalixarene as a route to a novel macrocyclic skeleton

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          Abstract

          The formation of a novel type of macrocyclic skeleton possessing meta- and para-bridging units can be achieved by S NAr cleavage of an easily accessible phenoxathiin-based thiacalix[4]arene.

          Abstract

          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 S NAr reaction.

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          Most cited references 23

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          Thiacalixarenes.

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            Chemistry of Thiacalixarenes

             Pavel Lhotak (2004)
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              S-Alkylation of Thiacalixarenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation

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                Author and article information

                Contributors
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                Journal
                CHCOFS
                Chemical Communications
                Chem. Commun.
                Royal Society of Chemistry (RSC)
                1359-7345
                1364-548X
                2020
                2020
                : 56
                : 1
                : 78-81
                Affiliations
                [1 ]Department of Organic Chemistry
                [2 ]University of Chemistry and Technology
                [3 ]Prague (UCTP)
                [4 ]166 28 Prague 6
                [5 ]Czech Republic
                [6 ]Department of Solid State Chemistry
                [7 ]UCTP
                [8 ]Laboratory of NMR Spectroscopy
                Article
                10.1039/C9CC08335A
                © 2020
                Product
                Self URI (article page): http://xlink.rsc.org/?DOI=C9CC08335A

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