Unprecedented cyclizations of calix[4]arenes with glycols under the Mitsunobu protocol, part 2.(1) O,O-and O,S-bridged calixarenes |
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Authors: | Csokai Viktor Grün Alajos Balázs Barbara Tóth Gábor Horváth Gyula Bitter István |
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Affiliation: | Budapest University of Technology and Economics, H-1521 Budapest, Hungary, and IVAX Drug Research Institute, Ltd., H-1325 Budapest, Hungary. |
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Abstract: | [reaction: see text] Cycloalkylations of p-tert-butylcalix[4]arene (CA) and p-tert-butylthiacalix[4]arene (TCA) with various aliphatic glycols were performed under the Mitsunobu protocol using the DEAD/TPP system. CA gave 1,3-dialkylated diols, while C(2)-C(10) glycols gave 1,2- and 1,3-bridged calixarenes. The reaction of TCA with C(2) diols afforded sulfonium phenoxide betaines via O,S-cyclization, which is the first example for the alkylation of the sulfide bridge. |
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