Monosodium salt of p-tert-butylcalix[4]arene in the reactions with electrophilic reagents. Synthesis and structure of monofunctionalized calix[4]arenes

Monosodium salt of p-tert-butylcalix[4]arene reacts with alkyl halides or aroyl chlorides in DMF formed the cone-shaped monoalkyloxycalix[4]arenes or 1,3-diacyloxycalix[4]arenes, respectively. Diacyloxycalix[4]arenes are easily transformed into monoacyloxycalix[4]arenes in the partial cone conformation by interaction with NaOMe. The influence of intramolecular hydrogen bonding on course of alkylation and acylation reactions as well as the structure of the synthesized compounds in solution and crystalline state are discussed.