106750-72-5Relevant articles and documents
CALIXARENES 12 THE SYNTESIS OF FUNCTIONALIZED CALIXARENES
Gutsche, C. David,Lin, Lee-Gin
, p. 1633 - 1640 (1986)
Procedures are described for the removal of the p-t-butyl groups from p-t-butylcalixarene, p-t-butylcalixarene, and p-t-butylcalixarene and the introduction of functional groups in their place.Although attempts to functionalize the p-positions of the calixarenes have generally failed, the corresponding methyl ethers are amenable to facile acetylation to provide syntheses of the p-acetyl-, p-carboxy-, and p-carbomethoxycalixarenes and calixarenes.Acetylation and benzoylation of calixarene and calixarene occur at the phenolic oxygens rather than the p-positions, leading under most reaction conditions to the completely O-substituted product.Calixarene reacts with benzoyl chloride in the presence of pyridine, however, to yield the tribenzoate.Conversion of the tribenzoate to the corresponding tribenzoyloxy monoallyl ether followed by a Claisen rearrangement and hydrolysis yields monoallylcalixarene, a compound of particular interest because of its potential for the synthesis of calixarenes containing a single substituent on the "upper rim".
