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, .
The reaction of carbon dioxide(CO2) with epoxides in the presence of pentavalent organoantimony compounds gave corresponding cyclic carbonates as a product in almost quantitative yields even under mild conditions.
In the cycloaddition of carbon dioxide to oxiranes to form cyclic carbonates in the presence of organometallic halides of group IVA, VA, and VIA, catalytic activities of organometallic halides are in the order Sb>Te>Sn>>Bi, Ge, and Si. An improvement of their catalytic activities is achieved by addition of an equimolar amount of Lewis base. In binary catalyst systems, the order of catalytic activities is in the order Sn>Te>Sb>>Bi, Ge, and Si. Organotin halide–base systems show the highest catalytic activity.
2-Hydroxymethylphenols have been prepared in good yield by reduction with sodium borohydride of the precursor aldehydes, obtained regiospecifically from reaction of phenols with paraformaldehyde in toluene containing stannic chloride and tri-n-butylamine. By contrast, reaction of phenols with either paraformaldehyde under anhydrous conditions or with aqueous formaldehyde results in formation of both the hydroxymethyl and the bishydroxymethyl derivatives. Cyclic acetals of the precursor aldehydes are readily accessible.
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