The oxidation of calix[4]arene dibenzoate 1 with chlorine dioxide yielded t
he corresponding calix[4]diquinone 2 and an intramolecular Michael-addition
product 3. Reaction of diquinone 2 with ethylene glycol under acidic condi
tions produced the half-protected ketal derivative 4. The removal of benzoa
te moieties from compound 4 in basic conditions produced a phenoxide anion,
which underwent intramolecular Michael-addition and yielded product 5. In
acidic ketal cleavage conditions, the ketal moieties of product 5 were remo
ved, but the intramolecular Michael-addition structure was maintained in th
e product 6. (C) 2001 Elsevier Science Ltd. All rights reserved.