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Titolo:
A NEW METHOD FOR REGIOSPECIFIC DEUTERIATION AND REDUCTION OF 5,10,15,20-TETRAPHENYLPORPHYRINS - NUCLEOPHILIC REACTION OF BOROHYDRIDE ION WITH 2-NITRO-5,10,15,20-TETRAPHENYLPORPHYRINS
Autore:
CROSSLEY MJ; KING LG;
Indirizzi:
UNIV SYDNEY,SCH CHEM SYDNEY NSW 2006 AUSTRALIA
Titolo Testata:
Journal of organic chemistry
fascicolo: 16, volume: 58, anno: 1993,
pagine: 4370 - 4375
SICI:
0022-3263(1993)58:16<4370:ANMFRD>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-PYRROLIC POSITION; 2-SUBSTITUTED 5,10,15,20-TETRAPHENYLPORPHYRINS; EFFICIENT SYNTHESIS; PROTON-TRANSFER; PORPHYRINS; TAUTOMERISM; METALLOPORPHYRINS; SPECTROSCOPY; SYSTEMS; CHLORINS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
37
Recensione:
Indirizzi per estratti:
Citazione:
M.J. Crossley e L.G. King, "A NEW METHOD FOR REGIOSPECIFIC DEUTERIATION AND REDUCTION OF 5,10,15,20-TETRAPHENYLPORPHYRINS - NUCLEOPHILIC REACTION OF BOROHYDRIDE ION WITH 2-NITRO-5,10,15,20-TETRAPHENYLPORPHYRINS", Journal of organic chemistry, 58(16), 1993, pp. 4370-4375

Abstract

New methods for specific reduction and deuteriation of 5,10,15,20-tetraarylporphyrins are reported. Free-base and metalated 2-nitroporphyrins are converted into the corresponding nitrochlorins 2-nitro-5,10,15,20-tetraphenyl-22H,24H-porphyrins) by reaction with borohydride followed by aqueous workup. These nitrochlorins may be readily converted into the denitrated chlorin by treatment with tributyltin hydride or intothe corresponding denitrated porphyrin by elimination of nitrous acidby heating or treatment with silica. Deuterium labeling studies show that the formation of nitrochlorin from nitroporphyrin involves attackby hydride at the beta-pyrrolic carbon next to that bearing the nitrogroup followed by protonation of the resultant nitronate in aqueous workup. Specific deuteriation at the beta-pyrrolic next to that previously occupied by a nitro group is readily achieved by borodeuteride ionreaction with a 2-nitroporphyrin (50 atom % deuterium incorporation) or with a 2-methoxy-3-nitroporphyrin (100 atom % deuterium incorporation).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/09/20 alle ore 05:04:50