Unexpected Formation of Disulfide-based Biscalix[4]arenes

0454479 - ÚCHP 2016 RIV GB eng J - Journal Article
Stejskal, F. - Cuřínová, Petra - Lhoták, P.
Unexpected Formation of Disulfide-based Biscalix[4]arenes.
Tetrahedron. Roč. 72, č. 5 (2016), s. 760-766. ISSN 0040-4020. E-ISSN 1464-5416
Institutional support: RVO:67985858
Keywords : calixarene * bridging reaction * complexation
OECD category: Organic chemistry
Impact factor: 2.651, year: 2016

Attempts at Pd-catalyzed bridging in sulfoxide-bearing calixarenes containing various substituents/n(phenyl, ethyl, pyrimidin-2-yl) gave the expected compound only in the case of the ethyl derivative./nHowever, the reaction of sulfoxides with BuLi revealed the ability of the pyrimidin-2-yl group to function unexpectedly as a leaving group. This enabled, depending on the reaction conditions, preparation of unique bis-calixarenes connected together via two sulfur atoms spacers: eSeSe, eS(O)eSe or eS(O)2eSe. As documented by 1H NMR titrations these compounds, otherwise not easily accessible by common synthetic methods, showed recognition ability towards selected cations of the N-methylpyridinium type.
Permanent Link: http://hdl.handle.net/11104/0255274