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Upper‐Rim Monofunctionalisation in the Synthesis of Triazole‐ and Disulfide‐Linked Multicalix[4]‐ and ‐[6]arenes
Author(s) -
Gardiner William H.,
Camilleri Matthew,
MartinezLozano Luis A.,
Bew Sean P.,
Stephenson G. Richard
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804755
Subject(s) - calixarene , supramolecular chemistry , covalent bond , chemistry , disulfide bond , alkylation , redox , combinatorial chemistry , catenane , dynamic covalent chemistry , thiol , triazole , polymer chemistry , organic chemistry , molecule , catalysis , biochemistry
Covalently linked multiple calixarenes are valued in supramolecular chemistry. This work reports an easy and versatile synthetic route to covalently linked double and triple calix[4]arene and calix[6]arenes by a novel DMF‐controlled selective alkylation of a convenient and readily available upper‐rim dimethylaminomethyl‐substituted tetrahydroxy and hexahydroxy calix[4]arene and ‐[6]arenes. Synthetic routes to upper‐rim functionalised redox active disulfide‐linked double‐, tetra‐ and peptidohybrid‐calixarenes employing either redox chemistry (CH 2 SH) or thiolates (CH 2 S − ) are also opened up from the same key starting material.