Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
INVESTIGATION OF A REVERSE APPROACH TO EXTENDED PORPHYRIN SYSTEMS - SYNTHESIS OF A 2,3-DIAMINOPORPHYRIN AND ITS REACTIONS WITH ALPHA-DIONES
Autore:
CROSSLEY MJ; KING LG; NEWSOM IA; SHEEHAN CS;
Indirizzi:
UNIV SYDNEY,SCH CHEM SYDNEY NSW 2006 AUSTRALIA
Titolo Testata:
Journal of the Chemical Society. Perkin transactions. I
fascicolo: 22, , anno: 1996,
pagine: 2675 - 2684
SICI:
0300-922X(1996):22<2675:IOARAT>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-PYRROLIC POSITION; EFFICIENT SYNTHESIS; SUBSTITUTION; ION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
27
Recensione:
Indirizzi per estratti:
Citazione:
M.J. Crossley et al., "INVESTIGATION OF A REVERSE APPROACH TO EXTENDED PORPHYRIN SYSTEMS - SYNTHESIS OF A 2,3-DIAMINOPORPHYRIN AND ITS REACTIONS WITH ALPHA-DIONES", Journal of the Chemical Society. Perkin transactions. I, (22), 1996, pp. 2675-2684

Abstract

A 2,3-diaminoporphyrin has been synthesised for the first time and its reaction with a-diones has been examined, Two regioselective routes to the precursor 2-amino-3-nitroporphyrins have been established. 2-Aminoporphyrins are directly nitrated on the porphyrin ring in the 3-position while 2-nitroporphyrins react with acylamide ions regioselectively at the 3-position and can be converted to the required 2-amino-3-nitroporphyrins by hydrolysis of the amide bond. 2,3-Diamino-5,10,15,20-tetraarylporphyrins are prepared by transfer hydrogenation of the corresponding 2-amino-3-nitroporphyrins but are relatively unstable. Electrochemical measurements show that 2,3-diaminoporphyrins are easily oxidised and this probably accounts for their instability. Condensation of the 2,3-diaminoporphyrin 29 with the alpha-diones benzil and cyclohexane-1,2-dione occurs readily and in good yield to give the ring annulated systems 31 and 32, respectively. Reaction with o-benzoquinone, however, Muses decomposition of the diaminoporphyrin 29 making 'reverse'synthesis of quinoxalinoporphyrins and related polyporphyrin systems much less attractive than the alternate approach involving condensation of a porphyrin-2,3-dione with o-phenylenediamine and related diamines.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 24/09/20 alle ore 20:12:42