The Wurtz-Fittig reaction in the preparation of C-silylated calixarenes

Paul F Hudrlik; Wondwossen D Arasho; Anne M Hudrlik

doi:10.1021/jo070660n

The Wurtz-Fittig reaction in the preparation of C-silylated calixarenes

J Org Chem. 2007 Oct 12;72(21):8107-10. doi: 10.1021/jo070660n. Epub 2007 Sep 12.

Authors

Paul F Hudrlik¹, Wondwossen D Arasho, Anne M Hudrlik

Affiliation

¹ Department of Chemistry, Howard University, Washington, DC 20059, USA. phudrlik@howard.edu

PMID: 17850095
DOI: 10.1021/jo070660n

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.