In the course of a study aimed at the investigation of edge-to-face arene-arene interactions, substituted benzylidenefluorenes 8-16 and benzylidene-1-azafluorenes 20-24 were synthesized as mixtures of E-Z-isomers. The full structural assignment of these compounds, performed by 2D NMR experiments, is described together with a study of their E-Z isomerization under equilibrating conditions. For compounds 8-16 no correlation was observed between the electron-donating or electron-withdrawing nature of the substituent groups and the E/Z equilibrium ratios. In the case of 20-24 the predominance of the E-isomers seems to depend exclusively on the N-lone pair-benzylidene ring electronic repulsion rather than on the nature of the pala substituent on the aromatic ring. (C) 1998 John Wiley & Sons, Ltd.

Synthesis and structural assignment of 2,4 '-disubstituted benzylidenefluorenes and 4 '-substituted benzylidene-1-azafluorenes / R. Annunziata, V. Molteni, L. Raimondi. - In: MAGNETIC RESONANCE IN CHEMISTRY. - ISSN 0749-1581. - 36:7(1998), pp. 520-528.

Synthesis and structural assignment of 2,4 '-disubstituted benzylidenefluorenes and 4 '-substituted benzylidene-1-azafluorenes

R. Annunziata
Primo
;
L. Raimondi
Ultimo
1998

Abstract

In the course of a study aimed at the investigation of edge-to-face arene-arene interactions, substituted benzylidenefluorenes 8-16 and benzylidene-1-azafluorenes 20-24 were synthesized as mixtures of E-Z-isomers. The full structural assignment of these compounds, performed by 2D NMR experiments, is described together with a study of their E-Z isomerization under equilibrating conditions. For compounds 8-16 no correlation was observed between the electron-donating or electron-withdrawing nature of the substituent groups and the E/Z equilibrium ratios. In the case of 20-24 the predominance of the E-isomers seems to depend exclusively on the N-lone pair-benzylidene ring electronic repulsion rather than on the nature of the pala substituent on the aromatic ring. (C) 1998 John Wiley & Sons, Ltd.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/181667
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 2
social impact