SELECTIVE ACYL AND ALKYLATION OF MONOBENZOYL P-TERT-BUTYLCALIX[4]ARENE

Several calixarene derivatives of ra-tert-butyl-25-(3,5-dinitrobenzoyl oxy)-26,27,28- trihydroxycalix[4]arene 2 were synthesized by the react ion of 2 with several acyl and alkylating agents in the presence of ba se such as pyridine and K2CO3 in THF. Acylation of monobenzoylated p-t ert-butylcalix[4]arene 2 yielded their corresponding 1,3-diacylated ca lix[4]arenes 3a-3g. On the other hand, alkylation of 2 produced a vari ety calix[4]arene derivatives such as 1,2- and 1,3-disubstituted calix [4]arenes 4a-4c, 4e-4f, or 1,2,4-trisubstituted calix[4]arene 4d. 1,2- Disubstituted calix[4]arenes are chiral. All derivatives exist as a co ne conformation based on NMR studies.