A variety of novel upper rim functionalized calix-arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix 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 calixarenes (5) were obtained in yields varying from 30 till 97%. The amidomethylation reactions were proven to be independent of the conformation of the calixarene.
|Journal||Journal für praktische Chemie|
|Publication status||Published - 1999|
- Synthetic methods
- electrophilic aromatic substitutions
- C-C coupling