Synthesis of calix[6]arenes partially functionalized at the upper rim

Alessandro Casnati, Laura Domiano, Andrea Pochini, Rocco Ungaro, Mar Carramolino, J. Oriol Magrans, Pedro M. Nieto, Javier Lopez-Prados, Pilar Prados, Javier de Mendoza, Rob G. Janssen, R.G. Janssen, Willem Verboom, David Reinhoudt

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Abstract

Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18¿94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these moieties allow the synthesis of macrocycles bearing amino, amido, hydroxymethyl, carboxy, cyano and chloromethyl functions which can be used for further transformation and preparation of new molecular receptors, based on calix[6]arenes, which have different geometries. Examples of di- and triquinones on the hexameric macrocycle are also reported.
Original languageUndefined
Pages (from-to)12699-12720
Number of pages22
JournalTetrahedron
Volume51
Issue number51
DOIs
Publication statusPublished - 1995

Keywords

  • METIS-106642
  • IR-12395

Cite this

Casnati, A., Domiano, L., Pochini, A., Ungaro, R., Carramolino, M., Magrans, J. O., ... Reinhoudt, D. (1995). Synthesis of calix[6]arenes partially functionalized at the upper rim. Tetrahedron, 51(51), 12699-12720. https://doi.org/10.1016/0040-4020(95)00826-T