Ferrocene derivatives. Part 24. Synthesis of dihydro-2-pyrindines and dihydro-3H-2-cyclopent[c]azepines by photolysis of their cyclopentadienyliron derivatives

Synthesis and Electrochemical Properties of N-(Ferrocenylmethyl)Aminobenzonitrile and N-(Ferrocenylmethyl)Nitroaniline Derivatives

“…Synthesis of N-(ferrocenylmethyl)nitroaniline and (ferrocenylmethylamino)benzonitrile derivatives, 3a X = 2-NO 2 , 3b X = 3-NO 2 , 3c X = 4-NO 2 , 3d X = 2-CN, 3e X = 3-CN, 3f X = 4-CN, 1 H NMR spectra for all compounds 3a-3f show five protons of the unsubstituted cyclopentadienyl ring (η5-C 5 H 5 ) as a strong singlet at δ 4.19-4.27. The protons of the methylene unit adjacent to the ferrocene moiety appear as a doublet (J = 4.72 to 5.13 Hz) at δ 3.96-4.14 often overlapping with the singlet of the (η5-C 5 H 5 ) ring.…”

“…1 H NMR spectra were recorded on BRUCKER AC 300 MHz spectrometer at 0°C, and the chemical shifts are reported in ppm relative to the central line of the triplet for CDCl 3 at 7.26 ppm. Coupling constants (J values) are reported in hertz (Hz), and spin multiplicities are indicated by the following symbols: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet).…”

“…In recent years, the design of new ferrocene derivatives has been of considerable interest, because of their utility in organic synthesis [1], catalysis [2], materials science [3,5], asymmetric synthesis [6], medicinal chemistry [7][8] and electrochemistry [9][10][11][12]. Our interests in ferrocene derivatives containing (methylamino)benzonitrile and N-methylnitroaniline groups arises from the fact that similar compounds such as N-(ferrocenylmethyl)benzene-carboxamide derivatives possess broad range of biological activities [13].…”

Experimental partition determination of octanol-water coefficients of ferrocene derivatives using square wave voltammetry techniques

“…The rapid advancement of ferrocene chemistry during the last 50 years, notably in areas related to biology and medicine [9][10][11][12][13], led us to turn our attention to the octanol-water partition coefficients of ferrocene derivatives. We herein present the experimental determination of this very important parameter that quantifies the lipophilicity of these derivatives and shows relationship between their structure and biological activity.…”

“…N-ferrocenylmethylaniline [12], ferrocenyl-2-nitrophenyl [13], N-ferrocenymethyl-N-phenylpropionamide [14], N'-ferrocenylmethyl-N'-phenylbenzohydrazide [15], ferrocenyl-4-nitrophenyl [16], Nferrocenymethyl-N-phenylacetamide [17], 1-ferrocenylethanol [18], N-Ferrocénylmethyl(2-cyano) aniline [19], 4-(ferrocenylmethylamino)benzonitrile [19] were all obtained according to literature procedures.…”