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β ‐Cyclodextrin‐Mediated Regioselective Hydrolysis of 5,10,15,20‐tetrakis[2,4‐bis(pivaloyloxy)phenyl]‐21 H ,23 H ‐porphine
Author(s) -
Matile Stefan,
Hansen Thorsten,
Stocker Achim,
Woggon WolfDietrich
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770422
Subject(s) - chemistry , tetraphenylporphyrin , regioselectivity , cyclodextrin , hydrolysis , porphyrin , stoichiometry , medicinal chemistry , spectroscopy , nuclear magnetic resonance spectroscopy , proton nmr , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
The four peripheral ester moieties of the title compound 5 are regioselectively hydrolyzed under mild conditions in the presence of β ‐cyclodextrin ( 10 ), providing a new entry to tetraphenylporphyrin derivatives with differently substituted Ph groups in the meso ‐positions. UV, 1 H‐NMR and mass spectroscopy of the inclusion complex 9 of 2,6‐ O ‐dimethyl‐β‐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).