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Titolo:
Extending the chemistry of [5,5,5,5]fenestranes - Eightfold peripheral functionalization of fenestrindanes
Autore:
Tellenbroker, J; Kuck, D;
Indirizzi:
Univ Bielefeld, Fak Chem, D-33501 Bielefeld, Germany Univ Bielefeld Bielefeld Germany D-33501 hem, D-33501 Bielefeld, Germany
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 8, , anno: 2001,
pagine: 1483 - 1489
SICI:
1434-193X(200104):8<1483:ETCO[->2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
PLANAR-TETRACOORDINATE CARBON; POLYNUCLEAR AROMATIC-HYDROCARBONS; ALPHA-AMINO-ACIDS; BENZOANNELATED CENTROPOLYQUINANES; MOLECULAR-STRUCTURE; SUBSTITUTED BENZENE; NONNATURAL TARGETS; ORGANIC-COMPOUNDS; DERIVATIVES; FENESTRANES;
Keywords:
arenes; aromatic substitution (multiple); fenestranes; indane compounds; polycycles (convex/concave);
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
87
Recensione:
Indirizzi per estratti:
Indirizzo: Kuck, D Univ Bielefeld, Fak Chem, Univ Str 25, D-33501 Bielefeld, Germany Univ Bielefeld Univ Str 25 Bielefeld Germany D-33501 eld, Germany
Citazione:
J. Tellenbroker e D. Kuck, "Extending the chemistry of [5,5,5,5]fenestranes - Eightfold peripheral functionalization of fenestrindanes", EUR J ORG C, (8), 2001, pp. 1483-1489

Abstract

Directed multiple functionalization of tetrabenzo[5.5.5.5]-fenestranes (fenestrindanes) at the molecular arene periphery has been achieved for the first time, starting from the fourfold bridgehead-methylated congener 2. In particular, 2,3,6,7,10,11,14,15-octabromofenestrindane (3) and 2,3,6,7,10,11,14,15-octaiodofenestrindane (7) have been synthesized as key intermediatesin excellent yields. Further eight-fold functionalized analogs, such as the corresponding octa(n-butyl) thioether 5 and the octacyanofenestrindane 8,are now accessible as well as other fenestrane hydrocarbons with an extended carbon framework, including the octakis-(phenylethynyl) and the octaphenyl derivatives 6 and 9, respectively. The S-4-symmetrical conformation of these fenestranes is evident from their H-1 and C-13 NMR spectra. It is suggested that, owing to their uniquely curved convex/concave molecular shape, fenestrindanes with eightfold peripheral functionalization could serve as unusual motifs for liquid crystal engineering and dendrimer chemistry, and for the construction of graphite cuttings bearing a saddle-like, three-dimensionally distorted core.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 21:03:21