Short communicationUnsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry
Graphical abstract
A new series of unsymmetrical cyrethrenyl and ferrocenyl azines monosubstituted and disubstituted derived from 5-nitrofurane have been prepared. They adopted an (E,E)-configuration in solution and in the solid stateas confirmed by X-ray structures of 1a and 2b.
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Acknowledgments
A.H.K. wishes to acknowledge FONDECYT-Chile (Projects 1150601 and 1110669) and D.I. Pontificia Universidad Católica de Valparaíso. J.G. wishes to acknowledge CONICYT and DEA for a Doctoral scholarship and D.I.-PUCV.
References (20)
- et al.
J. Organomet. Chem.
(2003) - et al.
J. Organomet. Chem.
(2014) - et al.
Appl. Organomet. Chem.
(2005)et al.Organometallics
(2003) - Cyrhetrenyl and ferrocenyl azines were synthesized according to previously published procedures [4]. Hydrazones...
- et al.
J. Mol. Struct.
(2007) - et al.
J. Organomet. Chem.
(2014) - et al.
J. Mol. Struct.
(2010) - et al.
RSC Adv.
(2014) - et al.
J. Organomet. Chem.
(2001)et al.J. Organomet. Chem.
(2002)et al.Can. J. Chem.
(1998)Mater. Lett.
(1997) - et al.
Can. J. Chem.
(2002)
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