Synthesis of 2-alkyl- and 2-carboxy-p-tert-butylcalix[4]arenes via the lithiation of tetramethoxy-p-tert-butylcalix[4]arene

P A Scully; T M Hamilton; J L Bennett

doi:10.1021/ol016346b

Synthesis of 2-alkyl- and 2-carboxy-p-tert-butylcalix[4]arenes via the lithiation of tetramethoxy-p-tert-butylcalix[4]arene

Org Lett. 2001 Aug 23;3(17):2741-4. doi: 10.1021/ol016346b.

Authors

P A Scully¹, T M Hamilton, J L Bennett

Affiliation

¹ Department of Chemistry and Biochemistry, Ebaugh Laboratories, Denison University, Granville, Ohio 43023, USA.

PMID: 11506623
DOI: 10.1021/ol016346b

Abstract

[reaction: see text]. 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.