Synthesis and Conformational Evaluation of p-tert-Butylthiacalix[4]arene-crowns


Leeuwen, Fijs W.B. van and Beijleveld, Hans and Kooijman, Huub and Spek, Anthony L. and Verboom, Willem and Reinhoudt, David N. (2004) Synthesis and Conformational Evaluation of p-tert-Butylthiacalix[4]arene-crowns. Journal of organic chemistry, 69 (11). pp. 3928-3936. ISSN 0022-3263

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Abstract:Bridging of p-tert-butylthiacalix[4]arene afforded 1,3-dihydroxythiacalix[4]arene-monocrown-5 (3b), 1,2-alternate thiacalix[4]arene-biscrown-4 and -5 (4a,b), and 1,3-alternate thiacalix[4]arene-biscrown-5 and -6 (5a,b), depending on the metal carbonates and oligoethylene glycol ditosylates used. Starting from 1,3-dialkylated thiacalix[4]arenes, the corresponding bridging reaction gave 1,3-alternate, partial-cone, and cone conformers 10-19, depending on the substituents present. Temperature-dependent studies revealed that the conformationally flexible 1,3-dimethoxythiacalix[4]arene-crowns 10a-c exclusively occupy the 1,3-alternate conformation. Demethylation exclusively gave the cone 1,3-dihydroxythiacalix[4]arene-crowns (3a,c), which could not be obtained by direct bridging of thiacalix[4]arene. The different structures were assigned on the basis of several X-ray crystal structures and extensive 2-D 1H NMR studies.
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Copyright:© 2004 American Chemical Society
Science and Technology (TNW)
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Official URL: S0022-3263(04)00122-7
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