| Abstract: | A variety of novel upper rim functionalized calix-4]arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix 4]arenes bearing propyl or ethoxyethyl substituents could be easily condensed with various N-methylol-amides and -imides under mild conditions. The resulting methyl-acetamido- ( 4a , 4b , 7a ), methylchloroacetamido ( 4c , 4d , 7b , 7c , 9 methylphthalimido ( 4e , 4f , 4h )and methylchloroacetamido methylphthalimido functionalized calix4]arenes ( 5 ) were obtained in yields varying from 30 till 97%. The amidomethylation reactions were proven to be independent of the conformation of the calix4]arene. |
