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- W2952364600 abstract "Various phenol-derived calix[4]arenes (3) bearing four hydroxy groups in the exo position have been prepared by uncatalyzed condensation of suitable dimers or tetramers with formaldehyde in xylene in yields up to 44%. The tetra-tert-butyl compound (3a) has been shown by X-ray analysis to adopt a regular cone conformation (nearly identical in shape with the endo isomer) with two intramolecular O−H···O hydrogen bonds, while the corresponding dimer (6c) prefers a conformation (not possible in the calixarene) with two intramolecular O−H···π(arene) interactions. Condensation of exo-calix[4]arenes 3f,g with free ortho positions (easily available by debutylation) with bisbromomethylated dimers gave annelated double (9) and triple (10) calixarenes consisting of endo- and exo-calix[4]arene substructures in yields up to 24% and 10%, respectively. Molecular dynamics calculations suggest that the exo-calixarene part in 9 is less mobile than the entirely flexible 3, while the endo-calixarene part shows a higher mobility than usual. A complete interconversion cone → cone is impossible, however, which enables the construction of inherently chiral molecules." @default.
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- W2952364600 date "1996-01-01" @default.
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- W2952364600 title "Annelated Calixarenes Composed of Calix[4]arenes with Hydroxy Groups in the <i>Endo</i> and <i>Exo</i> Position" @default.
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- W2952364600 doi "https://doi.org/10.1021/jo9511197" @default.
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