Synfacts 2006(5): 0447-0447  
DOI: 10.1055/s-2006-934435
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Naphthidines

Contributor(s): Timothy M. Swager, Scott Meek
C. Desmarets, B. Champagne, A. Walcarius*, C. Bellouard, R. Omar-Amrani, A. Ahajji, Y. Fort, R. Schneider*
Université Henri Poincaré, Vandoeuvre les Nancy, France
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Publikationsverlauf

Publikationsdatum:
21. April 2006 (online)

Significance

The synthesis along with electrochemical and spectral properties of seven novel N,N′-substituted naphthidines are reported. The synthesis presented proceeds first with Ni(0)-catalyzed amination of 1-chloronaphthalene, followed by TiCl4-induced oxidative dimerization. This pathway represents the first efficient method of accessing this class of compounds. Through cyclic voltammetry, UV-Vis and EPR spectrometry, it was noted that the naphthidines formed unusually stable di(radical cations). Theoretical studies carried out on the compounds showed that, while the neutral naphthidines prefer a twisted conformation, the oxidized versions adopt a more planar conformation in order to better delocalize the charge.