Synthesis of 2-Alkyl- and 2-Carboxy-p-tert-butylcalix[4]arenes via the Lithiation of Tetramethoxy-p-tert-butylcalix[4]arene

Autor: Scully, P. A., Hamilton, T. M., Bennett, J. L.
Zdroj: Organic Letters; August 2001, Vol. 3 Issue: 17 p2741-2744, 4p
Abstrakt: Tetramethoxy-p-tert-butylcalix[4]arene reacts readily with n-butyllithium to give a putative monolithiated intermediate that is substituted with alkyl halides and carbon dioxide to give in 60−75% yield conformationally mobile calix[4]arenes monosubstituted at the methylene bridge (2-position). 2-Alkyl- and 2-benzyl-substituted tetramethoxycalix[4]arenes are converted in 62−68% overall yield to the corresponding tetrahydroxy-p-tert-butylcalix[4]arenes by treatment with boron tribromide. The tetrahydroxy-p-tert-butylcalix[4]arenes exist in the cone conformation at room temperature in CDCl3 as judged by NMR spectroscopy.
Databáze: Supplemental Index