Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes

A.M.A. van Wageningen, André M.A. van Wageningen, Erwin Snip, Willem Verboom, David Reinhoudt, H. Boerrigter

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Abstract

Aminocalix[4]arenes 7-12 react with triphosgene and thiophosgene to the corresponding iso(thio)cyanate-functionalized calix[4]arenes 13-20. Carbamate- (21-25) and ureasubstituted calix[4]arenes (26,27) can be obtained via isocyanatocalix[4]arenes using a one-pot synthesis starting from the corresponding aminocalix[4]arenes in moderate to good yields. Isothiocyanate-functionalized calix[4]arenes 16, 18 react selectively with amines to the corresponding thioureas 28-31 in 59-83% yield. Reaction of isothiocyanate-functionalized calix[4]arenes 16, 19, 20 with cavitands 34, 38 gives 2:2 products 42-45 in 35-42% yield.
Original languageUndefined
Pages (from-to)2235-2245
JournalLiebigs Annalen
Issue number11
DOIs
Publication statusPublished - 1997

Keywords

  • METIS-106001
  • IR-11115

Cite this

van Wageningen, A. M. A., van Wageningen, A. M. A., Snip, E., Verboom, W., Reinhoudt, D., & Boerrigter, H. (1997). Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes. Liebigs Annalen, (11), 2235-2245. https://doi.org/10.1002/jlac.199719971110