Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes

L.C. Groenen, Leo C. Groenen, Bianca H.M. Ruel, Alessandro Casnati, P. Timmerman, Willem Verboom, Sybolt Harkema, Andrea Pochini, Rocco Ungaro, David Reinhoudt

Research output: Contribution to journalArticleAcademicpeer-review

128 Citations (Scopus)
64 Downloads (Pure)

Abstract

In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 4-6 can be isolated in 15-55 % from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.
Original languageUndefined
Pages (from-to)2675-2678
Number of pages4
JournalTetrahedron letters
Volume0
Issue number32
DOIs
Publication statusPublished - 1991

Keywords

  • METIS-106698
  • IR-12508

Cite this