The Wurtz-Fittig reaction in the preparation of C-silylated calixarenes |
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| Authors: | Hudrlik Paul F Arasho Wondwossen D Hudrlik Anne M |
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| Institution: | Department of Chemistry, Howard University, Washington, DC 20059, USA. phudrlik@howard.edu |
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| Abstract: | The Wurtz-Fittig reaction of tetraiodo calixarene 3 with Na/Me3SiCl in DME gave a mixture of tetrakis- and tris-silylated calixarenes (6 and 7). Tris(silyl) calixarene 7 was assigned the flattened cone conformation. A model study using p-bromoanisole and p-iodoanisole with Na/Me3SiCl gave the best results with p-bromoanisole in toluene. Attempts to extend this reaction to the tetrabromo calixarene 4 resulted in slow reactions giving mixtures of products. However, the Wurtz-Fittig reaction of the bromo benzyloxycalixarene 5 was faster, giving the debenzylated silyl ether 12. |
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