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Title

β-Cyclodextrin-Mediated Regioselective Hydrolysis of 5,10,15,20-tetrakis[2,4-bis(pivaloyloxy)phenyl]-21H,23H -porphine

Authors
Hansen, Thorsten
Stocker, Achim
Woggon, Wolf-Dietrich
Published in Helvetica Chimica Acta. 1994, vol. 77, no. 4, p. 1087-1095
Abstract The four peripheral ester moieties of the title compound 5 are regioselectively hydrolyzed under mild conditions in the presence of ß-cyclodextrin (10), providing a new entry to tetraphenylporphyrin derivatives with differently substituted Ph groups in the meso-positions. UV, 1H-NMR and mass spectroscopy of the inclusion complex 9 of 2,6-O-dimethyl-ß-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 the porphyrin with the small opening of the cavity (primary face).
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MATILE, Stefan et al. β-Cyclodextrin-Mediated Regioselective Hydrolysis of 5,10,15,20-tetrakis[2,4-bis(pivaloyloxy)phenyl]-21H,23H -porphine. In: Helvetica Chimica Acta, 1994, vol. 77, n° 4, p. 1087-1095. https://archive-ouverte.unige.ch/unige:6230

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Deposited on : 2010-04-20

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