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Unprecedented cyclisations of calix[4]arenes under the Mitsunobu protocol. Part 3: Thiacalix[4]crowns versus dimers |
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| Authors: | Viktor Csokai, Barbara Bal zs, G bor T th, Gyula Horv th,Istv n Bitter |
| Affiliation: | aDepartment of Organic Chemical Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary bTechnical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry, Budapest University of Technology and Economics, H-1111 Budapest, Hungary cIVAX Drug Research Institute Ltd, H-1325 Budapest, Hungary |
| Abstract: | Intermolecular couplings versus intramolecular ring closures were observed in the reaction of p-tert-butylthiacalix[4]arene and diethylene glycols affording dimers 2 and/or the inherently chiral 1,2-thiacalix[4]crown-3 derivatives 5 under the Mitsunobu protocol. The enantiomeric separation of 5a was achieved by chiral HPLC. The reaction of thiacalix[4]monocrowns 1 with diethylene glycols failed to give crowned thiacalix-tubes 7, instead biscrowns 8 were formed. Partially alkylated double thiacalix[4]arenes 10, 11 were obtained via the base promoted alkylations of a thiacalixarene dimer 2a containing diethyleneoxy linkers. |
| Keywords: | Thiacalix[4]arenes Cyclisations Thiacalix[4]crowns Dimers Mitsunobu reaction |
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