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Synthesis of Functional meso-Aryl Porphomonomethenes and Porphodimethenes: Application to the Preparation of a Chiral Calix[4]phyrin Dimer
journal contribution
posted on 2004-11-12, 00:00 authored by Markéta Bernátková, Bruno Andrioletti, Vladimír Král, Eric Rose, Jacqueline VaissermannReaction of 5,5-dimethyldipyrromethane (1) with
electron-deficient aryl aldehydes in the presence of BF3−Et2O and NH4Cl in propionitrile constitutes efficient, easy
access to unprecedented, functional porphomonomethenes
together with the expected porphodimethenes (calix[4]phyrins). Alternatively, when the reaction was carried out
in CH2Cl2 in the presence of an acid and Florisil, the
expected bis-arylcalix[4]phyrin was isolated in 41% yield,
while no scrambled macrocycle was detected. After reduction
of the nitro function, porphomonomethene 9 was efficiently
condensed with the binaphthyl diacyl chloride (10) leading
to the first chiral calix[4]phyrin dimer (11) that exhibits a
moderate enantiorecognition toward the enantiomers of
malic acid.
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exhibitbinaphthyl diacyl chlorideCalixmacrocycleAryl PorphomonomethenespresenceporphodimetheneBFApplicationaccesscalixenantiomernitro functionCH 2 Cl 2propionitrilealdehydeSynthesiFlorisilChiraldimethyldipyrromethanePreparationmalic acidPorphodimetheneDimerchiralporphomonomethene 9Functional m esoNH 4 ClarylEtenantiorecognitiondimer
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