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Titolo:
Structural features of primary 6-aminopentafulvenes and some of their derivatives
Autore:
Kunz, D; Frohlich, R; Erker, G;
Indirizzi:
Univ Munster, Inst Organ Chem, D-48149 Munster, Germany Univ Munster Munster Germany D-48149 rgan Chem, D-48149 Munster, Germany
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 18, , anno: 2001,
pagine: 3531 - 3536
SICI:
1434-193X(200109):18<3531:SFOP6A>2.0.ZU;2-P
Fonte:
ISI
Lingua:
ENG
Soggetto:
METALLOCENE COMPLEXES; OLEFIN POLYMERIZATION; 2+2 CYCLOADDITION; ANSA-METALLOCENE; CYCLOPENTADIENYL; CATALYST; LIGANDS; ROUTE; ACTIVATION; CHEMISTRY;
Keywords:
fulvene structures; aminopentafalvenes; substituent effects;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
41
Recensione:
Indirizzi per estratti:
Indirizzo: Erker, G Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany Univ Munster Corrensstr 40 Munster Germany D-48149 ster, Germany
Citazione:
D. Kunz et al., "Structural features of primary 6-aminopentafulvenes and some of their derivatives", EUR J ORG C, (18), 2001, pp. 3531-3536

Abstract

Starting from 6-amino-6-methylpentafulvene (2) 'ortho"-C-acylation or N-acylation can be achieved selectively. Treatment of 2 with phthaloyl-protected amino acid chlorides derived from alanine (3a) or valine (3b) leads exclusively to the formation of the "ortho"-C-acylated derivatives 4, isolated as racemates. Optically active N-acylated products 7 were prepared by coupling 5, obtained by NH deprotonation of 2, with the 1-hydroxybenzotriazole (HOBt) active-esters of alanine (6a), valine (6b), or leucine (6c) bearing benzylprotected amino groups, Complexes 2, 4a, 4b, and 7a were characterized by X-ray diffraction. Electron-withdrawing groups attached at the "ortho" ring position lead to a shortening of the external C6-N bond, whereas electron-withdrawing groups bound to the nitrogen atom lead to an elongation of the C6-N bond, compared to the parent system 2.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/10/20 alle ore 05:01:22