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Titolo:
CONFORMATIONAL ASSIGNMENT, ABSOLUTE-CONFIGURATION, AND CHIRAL SEPARATION OF ALL THE STEREOISOMERS CREATED BY THE COMBINED PRESENCE OF STEREOGENIC CENTERS AND STEREOGENIC CONFORMATIONAL AXES IN A HIGHLY HINDERED 1,5-NAPHTHYL SULFOXIDE
Autore:
CASARINI D; LUNAZZI L; GASPARRINI F; VILLANI C; CIRILLI M; GAVUZZO E;
Indirizzi:
UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,VIALE RISORGIMENTO 4 I-40136 BOLOGNA ITALY UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI CHIM & TECNOL SOSTANZE BIOL AT I-00185 ROME ITALY CNR,IST STRUTTURIST CHIM I-00016 MONTEROTONDO ITALY
Titolo Testata:
Journal of organic chemistry
fascicolo: 1, volume: 60, anno: 1995,
pagine: 97 - 102
SICI:
0022-3263(1995)60:1<97:CAAACS>2.0.ZU;2-P
Fonte:
ISI
Lingua:
ENG
Soggetto:
DYNAMIC NMR; STEREODYNAMICS; RESOLUTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
10
Recensione:
Indirizzi per estratti:
Citazione:
D. Casarini et al., "CONFORMATIONAL ASSIGNMENT, ABSOLUTE-CONFIGURATION, AND CHIRAL SEPARATION OF ALL THE STEREOISOMERS CREATED BY THE COMBINED PRESENCE OF STEREOGENIC CENTERS AND STEREOGENIC CONFORMATIONAL AXES IN A HIGHLY HINDERED 1,5-NAPHTHYL SULFOXIDE", Journal of organic chemistry, 60(1), 1995, pp. 97-102

Abstract

The presence of two stereogenic centers and of two stereogenic conformational axes in thyl-1,5-bis(2-methyl-2-propylsulfinyl)naphthalene (1) entails the existence of 10 stereoisomers. In particular, both the meso form (1a) and the racemic form (1b) are constituted by three atropisomers; in the case of the latter (1b) each of them entails a pair ofenantiomers (total of six species), whereas owing to the symmetry only one of the three atropisomers of the meso form (1a) yields a pair ofenantiomers (a total of four species). Despite the low conformationalinterconversion barrier (18.5 kcal/mol) all of them have been separated by low temperature (-45 degrees C) chiral HPLC. Their configurational and conformational assignment has been achieved by a combined use of NMR (both in solution and solid state) and on-line CD-detected chiral HPLC. The single crystal X-ray diffraction yielded the absolute configuration of one of the stereoisomers ((ZR,ER)-1b) from which all the others could be obtained by CD relationship.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/09/20 alle ore 15:33:46