Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
Synthesis and isomerization of arene oxide metabolites of phenanthrene, triphenylene, dibenz[a,c]anthracene and dibenz[a,h]anthracene
Autore:
Balani, SK; Brannigan, IN; Boyd, DR; Sharma, ND; Hempenstall, F; Smith, A;
Indirizzi:
Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland Queens Univ Belfast Belfast Antrim North Ireland BT9 5AG m, North Ireland
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 9, , anno: 2001,
pagine: 1091 - 1097
SICI:
1472-7781(2001):9<1091:SAIOAO>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
ABSOLUTE-CONFIGURATION; CIS-DIHYDRODIOLS; THEORETICAL PREDICTIONS; PSEUDOMONAS-PUTIDA; CRYSTAL-STRUCTURE; NON-K; BENZANTHRACENE; RACEMIZATION; DIOXYGENASE; RESOLUTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
40
Recensione:
Indirizzi per estratti:
Indirizzo: Boyd, DR Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland Queens Univ Belfast Belfast Antrim North Ireland BT9 5AG Ireland
Citazione:
S.K. Balani et al., "Synthesis and isomerization of arene oxide metabolites of phenanthrene, triphenylene, dibenz[a,c]anthracene and dibenz[a,h]anthracene", J CHEM S P1, (9), 2001, pp. 1091-1097

Abstract

Dibenz[a,h]anthracene 3,4-oxide 5A(RS), synthesised from the enantiopure dibromoMTPA precursor 9A(RRS*), was found to have totally racemized and to be accompanied by benz[5,6]anthra[1,2-b]oxepine 11A. Phenanthrene 3,4-oxide 5B(RS), obtained from the enantiopure bacterial metabolite cis-3,4-dihydroxy-3,4-dihydrophenanthrene 12B by a modified synthetic approach involving the chlorohydrin ester 16B, was observed to racemize spontaneously at ambienttemperature. Dibenz[a,h]anthracene 3,4-oxide 5A(RS)/5A(SR), phenanthrene 3,4-oxide 5B(RS)/5B(SR), triphenylene 1,2-oxide 5C(RS)/5C(SR), and dibenz[a,c]anthracene 1,2-oxide 5D(RS)/5D(SR), obtained from the corresponding racemic cis-tetrahydrodiol precursors 14A-14D by the new method, were obtained without any evidence of the formation of benz[5,6]anthra[1,2-b]oxepine 11A, naphth[1,2-b]oxepine 11B, phenanthro[10,9-b]oxepine 11C, or benz[3,4]anthra[1,2-b]oxepine 11D isomers respectively. The total racemization of arene oxide 5A(RS) and formation of oxepine 11A from the bromoMTPA precursor 8A(RRS*) are in accord with earlier PMO predictions based on resonance energy considerations. Photoisomerization of arene oxides 5A(RS)/5A(SR), 5C(RS)/5C(SR), and 5D(RS)/5D(SR) was found to yield the corresponding oxepines 11A, 11C, and 11D.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/09/20 alle ore 06:30:44