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

André M.A. van Wageningen, Erwin Snip, Willem Verboom, David N. Reinhoudt*, Harold Boerrigter

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

29 Citations (Scopus)
62 Downloads (Pure)

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 languageEnglish
Pages (from-to)2235-2245
JournalLiebigs Annalen
Volume1997
Issue number11
DOIs
Publication statusPublished - 1997

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