First synthesis of adamantylated thiacalix[4]arenes
β Scribed by Elvira Shokova; Victor Tafeenko; Vladimir Kovalev
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 128 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
p-(1-Adamantyl)thiacalix[4]arene was synthesized both by condensation of p-(1-adamantyl)phenol with sulfur in the presence of NaOH and by alkylation of p-H -thiacalix[4]arene with 1-adamantanol in trifluoroacetic acid. Using the latter method, the first thiacalix[4]arene carboxylated at the upper rim was obtained from p-H-thiacalix [4]arene and 3-carboxy-1-adamantanol. The X-ray structural analysis revealed that p-(1-adamantyl)thiacalix [4]arene adopts a cone conformation leading to an inclusion complex with chloroform under the conditions of crystallization.
π SIMILAR VOLUMES
Thiacalix[4]arenes were alkylated using procedures well established in 'classical' calixarene chemistry (PrI/K 2 CO 3 /acetone or PrI/NaH/DMF) to reveal conformational preferences in the thiacalixarene series. Surprisingly, the conformer distribution of tetraalkylated products is different from that
A direct nitration of the upper rim of thiacalix [4]arenes is not possible due to the undesirable oxidation of the sulphur atoms during the nitration step leading to very complicated reaction mixtures. On the other hand, thiacalix[4]arene derivatives can be at first transformed intentionally to the
Upper rim bromination of thiacalix [4]arene has been achieved for the first time using a distally disubstituted thiacalix[4]arene as a starting material. Depending on the bromine:thiacalix[4]arene ratios, the corresponding dibromo-and tetrabromo derivatives were obtained which opens the door for sub
The synthesis of tetrathiacalix [4]arene was achieved by the detertiobutylation of p-tert-butyltetrathiacalix[4]arene. X-ray diffraction studies revealed that in the solid state whereas p-tert-butyltetrathiacalix[4]arene forms inclusion complexes with solvent molecules, tetrathiacalix[4]arene under