BETA-CYCLODEXTRIN-MEDIATED REGIOSELECTIVE HYDROLYSIS OF RAKIS[2,4-BIS(PIVALOYLOXY)PHENYL]-21H,23H-PORPHINE

The four peripheral ester moieties of the title compound 5 are regiose lectively hydrolyzed under mild conditions in the presence of beta-cyc lodextrin (10), providing a new entry to tetraphenylporphyrin derivati ves with differently substituted Ph groups in the, meso-positions. UV, H-1-NMR and mass spectroscopy of the inclusion complex 9 of 2,6-O-dim ethyl-beta-cyclodextrin (12) and 5 indicate a stoichiometry of 2:1 for 10/5. Moreover, calculations confirm NOE experiments consistent with the fact that the cyclodextrins 10 and 12 approach the Ph groups of th e porphyrin with the small opening of the cavity (primary face).