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Titolo:
Synthesis of highly optically active polysulfoxides by asymmetric oxidation of polysulfides
Autore:
Oyama, T; Chujo, Y;
Indirizzi:
Kyoto Univ, Dept Polymer Chem, Grad Sch Engn, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 Sch Engn, Sakyo Ku, Kyoto 6068501, Japan
Titolo Testata:
MACROMOLECULES
fascicolo: 23, volume: 32, anno: 1999,
pagine: 7732 - 7736
SICI:
0024-9297(19991116)32:23<7732:SOHOAP>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOMERICALLY PURE SULFOXIDES; (SALEN)MANGANESE(III) COMPLEX; ORGANOSULFUR COMPOUNDS; CHIRAL SULFOXIDES; GENERAL-ROUTE; SULFIDES; OXAZIRIDINES; CHEMISTRY; REAGENTS; CATALYST;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
42
Recensione:
Indirizzi per estratti:
Indirizzo: Chujo, Y Kyoto Univ, Dept Polymer Chem, Grad Sch Engn, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 , Sakyo Ku, Kyoto 6068501, Japan
Citazione:
T. Oyama e Y. Chujo, "Synthesis of highly optically active polysulfoxides by asymmetric oxidation of polysulfides", MACROMOLEC, 32(23), 1999, pp. 7732-7736

Abstract

Novel highly optically active polysulfoxides having chiral sulfinyl groupsin the main chain were prepared by asymmetric oxidation of the corresponding polysulfides by using chiral N-sulfonyl-oxaziridine (6). The polysulfoxide with the enantiomeric excess up to 91% ee was obtained in good chemoselectivity when the reaction was carried out with 1 equiv of (-)-N-sulfonyloxaziridine, (-)-6, in chloroform at room temperature followed by reflux. The enantiomeric excess was estimated from the C-13 NMR spectrum, and the stereochemistry at the sulfur atom was speculated by comparison of CD spectra ofthe polysulfoxides with that of the model compound ((S)-p-tolyl methyl sulfoxide). This asymmetric oxidation is the first example of introduction of chirality in good enantioselectivity into the main chain of a polymer by polymer reaction, that is, the first example of the control of "tacticity'' by polymer reaction. In fact, the shift of the glass transition temperature of the polysulfoxide was observed depending on the change of tacticity of the polymer. The obtained polymer is regarded as one of the first examples of the polymers having heteroatom chirality in the main chain.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/07/20 alle ore 22:09:14