Novel upper rim punctionalizations of calix[4]arenes using the Tscherniac-Einhorn amidomethylation reaction

A variety of novel upper rim functionalized calix-[4]arenes have been synth esized, using the Tscherniac-Einhorn amidomethylation reaction. Partially o r fully alkylated calix [4]arenes bearing propyl or ethoxyethyl substituent s could be easily condensed with various N-methylol-amides and -imides unde r mild conditions. The resulting methyl- acetamido- (4a, 4b, 7a), methylchl oroacetamido (4c, 4d, 7b, 7c, 9 methylphthalimido (4e, 4f, 4h) and methylch loroacetamido methylphthalimido functionalized calix[4]arenes (5) were obta ined in yields varying from 30 till 97%. The amidomethylation reactions wer e proven to be independent of the conformation of the calix[4]arene.