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Alkylation of thiacalix[4]arenes

✍ Scribed by Pavel Lhoták; Michal Himl; Ivan Stibor; Hana Petřı́čková

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
312 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 of calix[4]arene. The 1,3-alternate conformers are well accessible in high yields (>60%) while the cone conformation forms only in very low yields (<20%). Moreover, the conformational outcome of the alkylation strongly depends on the upper rim substitution (tert-butyl versus H).

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Upper Rim Substituted Thiacalix[4]arenes
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Nitration of thiacalix[4]arene derivativ
Nitration of thiacalix[4]arene derivatives
✍ Pavel Lhoták; Jiri Svoboda Jr.; Ivan Stibor; Jan Sykora 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 205 KB

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

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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