Synthesis of a deep-cavity thiacalix[4]arene

Chemistry of Thiacalixarenes

“…[68,69] Similar binding modes have also been proposed for metal complexation by thiacalix [6]arene (4). [76] Recently, many X-ray structures of thiacalixarene complexes with various transition metals have appeared in the literature.…”

“…A similar procedure has been used for the preparation of the corresponding tert-octyl derivative 6, [4] but unfortunately the yield of this compound was much lower (14 %). Very recently, thiacalix [4]arenes 7 and 8 were prepared in 20Ϫ28 % yields under similar reaction conditions, starting from p- (1-adamantyl)phenol [5] and biphenyl-4-ol, [6] respectively. Whereas four-membered thiacalixarenes are now accessible in multi-gram amounts, the higher thiacalixarenes 3 and 4 have only been isolated as by-products (trace amounts and 0.03 %, respectively) from a direct condensation procedure.…”

Self‐Assembly from Two‐Dimensional Layered Networks to Tetranuclear Structures: Syntheses, Structures, and Properties of Four Copper–Thiacalix[4]arene Compounds

“…Materials and Measurements: p-tert-Butylthiacalix [4]arene and pphenylthiacalix [4]arene were synthesized by literature methods, [19,11] and the other reagents were purchased from commercial sources and used as received. IR spectra (KBr pellets) were obtained with a Bruker Vertex 70 spectrometer.…”

Heteroatom-Containing, Carbon-Bridged Calix[4]arene, Thiacalix[4]arene and Sulfonamide Bridged Calix[4]arene

“…[41], with a very low yield. Pavel Lhoták reported the synthesis of a deep-cavity thiacalix[4]arene derivative 61 from the condensation of biphenyl-4-ol with element sulfur at 230 o C for 6 h [42]. The method involved heating p-tert-butyl phenol and sulfur to 230 o C for 4h in the presence of base, which gave thiacalix[4]arene in a yield of 54% together with small amounts of p -t e r tbutylcalix[5]arene and p-tert-butylcalix [6]arene.…”