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Formation of upper rim acylated calix[4]arenes using a sacrificial zinc anode |
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| Authors: | Alain Louati Rame Vataj Manuel Lejeune |
| Institution: | a Laboratoire d’Electrochimie Analytique, ENSCMu, UHA, 3 rue Alfred Werner, F-68093 Mulhouse Cedex, France b Laboratoire de Spectrométrie de Masse, Institut de Chimie (B6c), Université de Liège, Allée de la Chimie 17, B-400 Liège, Belgium c Laboratoire de Chimie Inorganique Moléculaire, Université Louis Pasteur, UMR 7513, F-67008 Strasbourg Cedex, France |
| Abstract: | A straightforward electrosynthetic method is described, which allows upper rim acylation of non-p-halogenated calix4]arenes. For example, a solution of tetrapropoxycalix4]arene 4 was electrolysed in the presence of ZnBr2 in an undivided cell fitted with a sacrificial zinc anode using pure acetonitrile as solvent, yielding an organozinc species, which was then treated with acetyl chloride in the presence of a palladium catalyst to afford 5,11-diacetyl-25,26,27,28-tetrapropoxycalix4]arene 5 in ca. 35% yield after workup. |
| Keywords: | Sacrificial zinc anode Calix[4]arenes Upper rim acylation Electrosynthesis |
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