Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
The synthesis and spectroscopic characterisation of chiral meso-tetraarylmetalloporphyrins bearing meso-pentafluorophenyl groups
Autore:
Foxon, SP; Smith, JRL; OBrien, P; Reginato, G;
Indirizzi:
Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England Univ York York N Yorkshire England YO10 5DD O10 5DD, N Yorkshire, England
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
fascicolo: 7, , anno: 2001,
pagine: 1145 - 1153
SICI:
1472-779X(2001):7<1145:TSASCO>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
CATALYZED ASYMMETRIC EPOXIDATION; ENANTIOSELECTIVE EPOXIDATION; PORPHYRINS; OLEFINS; ALKENES; METAL; METALLOTETRAARYLPORPHYRINS; TETRAPHENYLPORPHYRINS; METALLOPORPHYRINS; REACTIVITY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
49
Recensione:
Indirizzi per estratti:
Indirizzo: Smith, JRL Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England Univ York York N Yorkshire England YO10 5DD Yorkshire, England
Citazione:
S.P. Foxon et al., "The synthesis and spectroscopic characterisation of chiral meso-tetraarylmetalloporphyrins bearing meso-pentafluorophenyl groups", J CHEM S P2, (7), 2001, pp. 1145-1153

Abstract

The successful synthesis of 5,10,15,20-tetrakis[(R,R)-2,6-bis(1-phenylbutoxy)phenyl]porphyrin, with (R)-1-phenylbutoxy substituents on each of the eight ortho-positions, by a 2+2 approach via meso-[(R,R)-2,6-bis(1-phenylbutoxy)phenyl]dipyrromethane rather than a one-pot condensation of (R,R)-2,6-bis(1-phenylbutoxy)benzaldehyde with pyrrole, is described. The synthesis hasalso been modified using meso-(pentafluorophenyl)dipyrromethane to preparefour further chiral porphyrins containing one, two (cis and trans) and three pentafluorophenyls in place of the bis(phenylbutoxy)phenyl groups. The cross-coupling of the two dipyrromethanes with pentafluorobenzaldehyde gave as one of the products the unexpected cis-disubstituted 5,10-bis(pentafluorophenyl)-15,20-bis[(R,R)-2,6-bis(1-phenylbutoxy)phenyl]porphyrin. It seems likely that the formation of the latter compound involves the acid-catalysed reversion of the dipyrromethane synthesis. Both faces of each of the porphyrins are chiral and equivalent in this way the wasteful formation and time-consuming separation of atropisomers is avoided. Four iron(III) and one manganese(III) complex of these porphyrins have been prepared. The H-1 and F-19 NMR spectra of the series of porphyrin ligands reveal some interesting structure- and symmetry-dependent splitting patterns and trends which are used to confirm the identities of the compounds. In particular, the H-1 NMR couplings of the beta -pyrrole hydrogens are very diagnostic of the substitution patterns of the meso-aryl groups on the porphyrin ring.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/09/20 alle ore 20:04:00