Chemical transformations of partially adamantylated calix[4]arenes at
the upper rim are described. Starting from triadamantylated calix[4]ar
ene, it is possible to obtain adamantane-containing macrocycles with f
ormyl, acyl, sulfo, ate, 3-substituted 1-adamantyl, and dialkylaminome
thyl groups at the upper rim. Synthesis of a new type of double adaman
tane containing calix[4]arenes is also reported.