Formaldehyde polymers, 29. Isolation and characterization of calix[5]arene from the condensation product of 4‐tert‐butylphenol with formaldehyde

Abstract

Recently, there has been a growing interest in the reactions of p-substituted phenols with formaldehyde in the presence of basic catalysts, leading to cyclic oligomers ("calixarenes"b)) in good yields. From the reaction products of 4-tert-butylphenol with formaldehyde, calii[4, 6, and 8larenes and bishomooxacalix[4]arene have been isolated and confirmed".This article reports on the isolation of calix[5]arene from the reaction product of 4-tert-butylphenol with formaldehyde in tetralin in the presence of potassium tertbutoxide. Experimental PartGeneral: IR spectra were obtained with KBr pellets on a Hitachi 260-30 spectrophotometer, 'H NMR spectra on a JEOL PS-100 spectrometer with tetramethylsilane as internal standard, and "C NMR spectra on a JEOL FX-60 spectrometer. Chemical shifts are reported as 6 values in parts per million relative to deuteriochloroform (6 = 78.02) as an internal standard. Mass spectra were obtained on a Hitachi RUM-6 mass spectrometer operating at 70 eV. Molecular weight was determined with a Hitachi-Perkin-Elmer 115 vapor pressure osmometer apparatus, using CHCl, .

Cation complexation with p-tert-butylcalix[5]arene pentacarboxylic acid derivative: An allosteric regulation of the first metal ion for stepwise extraction of the second ion

“…1 H-NMR (300 MHz, CDCl 3 , TMS) d 1. 25 [5]arene (2). The procedure adopted for the synthesis of 2 is the one previously employed for the synthesis of the tetrameric analogue.…”

“…6% yield. 2 Dumazet et al synthesized it in a two step process via the ring opening of p-tert-butyldihomooxacalix [4]arene and addition of an equimolar quantity of p-tertbutylphenol in the presence of 0.17 mole ratio KOH. 3a They reported a 32% yield (HPLC) of the cyclic pentamer from p-tertbutyldihomooxacalix [4]arene, which, in turn, was obtained in 24% yield from p-tert-butylphenol.…”

Synthesis and structures of O-anthrylmethyl-substituted hexahomotrioxacalix[3]arenes

“…The synthesis of 7,15,23-tri-tert-butyl-2,4,10,12,18,20-hexahomo-3,11,19-trioxacalix [3]arene (1H 3 ) was carried out according to the reported procedure [34].…”

The Trouble with Five: New Synthetic Strategies toward C5 -Symmetric Pillar[5]arenes and Beyond

“…7 Among basic chemical building blocks, two-, three-, four-, and six-fold symmetric molecules prevail, whereas organic species with a C 5 -axis remain few and far between (Figure 1), even though five-fold symmetry 8 is not uncommon in the biological world. Other than corannulene 9 and fuller-ene 10 derivatives, the line of five-fold symmetric organic compounds mainly consists of macrocycles containing five repetitive units, for example, calix [5]arene, 11 five-membered cyclodextrin (CD5), 12 and cucurbit [5]uril. 13 More recently, pillar [5]arene, 14 Singapore pentamer, 15 campestarene, 16 cyanostar, 17 and [5]cycloparaphenylene 18 also came into view.…”