Ferrocene studies. VI. Some heterocyclic derivatives of ferrocene

Popp, Frank D.; Moynahan, E. Bradley

doi:10.1002/jhet.5570070352

Cited by 11 publications

(2 citation statements)

References 3 publications

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“…123-125°C (heptane; lit. 2 (4) A solution of chlorocarbonylferrocene (519 mg, 2.1 mmol) in dry pyridine (3 ml) was added to a mixture of hydrazine hydrate (48 µl, 1.0 mmol) and pyridine (5 ml) while cooling on ice. The cooling bath was removed and the resulting mixture was stirred at room temperature overnight, and then evaporated under vacuum.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, crystal structures and electrochemistry of ferrocenyl-substituted 1,3,4-oxadiazoles

Tauchman¹,

Trnka²,

Cı́sařová³

et al. 2010

Collect. Czech. Chem. Commun.

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Two ferrocenyl-substituted 1,3,4-oxadiazoles, 2-ferrocenyl-1,3,4-oxadiazole (1) and 2,5-diferrocenyl-1,3,4-oxadiazole (2), have been prepared from the corresponding hydrazides, (ferrocenecarbonyl)hydrazine (3) and 1,2-bis(ferrocenecarbonyl)hydrazine (4), and characterized by conventional spectroscopic methods (IR, NMR, MS) and elemental analyses. The solid-state structures of 1, 2 and 4 have been determined by single-crystal X-ray diffraction analysis. The redox behavior of 1 and 2 was studied by electrochemical methods. Compound 1 underwent a reversible one-electron oxidation attributed to the ferrocene/ ferrocenium couple (E o ′ = +0.28 V vs ferrocene/ferrocenium). On the other hand, compound 2 showed two closely separated anodic waves corresponding to two consecutive redox changes, indicating some degree of electronic communication between the ferrocenyl moieties in positions 2 and 5 at the 1,3,4-oxadiazole ring. Substituted 1,3,4-oxadiazoles have found various applications as biologically active compounds and building blocks for materials chemistry 1 . Despite their frequent use in the latter field, there is only little known about the redox-active, ferrocenyl-modified 1,3,4-oxadiazoles. Indeed, the archetypal compounds, 2-ferrocenyl-1,3,4-oxadiazole (1) (ref. 2 ) and 2,5-diferrocenyl-1,3,4-oxadiazole (2) (ref. 3 ) have already been reported. The former compound was obtained by the conventional condensation of ferrocenecarbohydrazide, FcCONHNH 2 (3; Fc = ferrocenyl), with triethyl orthoformate, whereas the diferrocenylated compound 2 and some related compounds, including the unsymmetric derivative (Ph/Fc), were obtained by POCl 3 -mediated cyclization of the respective 1,2-diacylhydrazines,

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Section: Methodsmentioning

confidence: 99%

Synthesis, crystal structures and electrochemistry of ferrocenyl-substituted 1,3,4-oxadiazoles

Tauchman¹,

Trnka²,

Cı́sařová³

et al. 2010

Collect. Czech. Chem. Commun.

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“…Although the N-heterocyclic ferrocenes dealt with in this section are simple, their coordination structures vary, accompanying the variation of the M:L ratios. Ferrocenes with bulky N-heterocycles, such as indole [47], benzimidazole [37], perimidine [48], quinoline [30,32,39,43], and quinoxaline [33][34][35][36]38], also act as monodentate ligands; however, their metal complexes are fewer.…”

Section: N-heterocyclic Ferrocenes That Produce Monodentate Complexesmentioning

confidence: 99%

Discrete metal complexes from N-heterocyclic ferrocenes: Structural diversity by ligand design

Horikoshi

2013

Coordination Chemistry Reviews

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The aim of this review is to provide an overview of the structures of discrete metal complexes with N-heterocyclic ferrocenes, based on their crystal structures. These N-heterocyclic ferrocenes act as versatile ligands for the construction of metal complexes with unique structures, owing to the π•••π interaction between the N-heterocycles and conformational flexibility of the ferrocenyl moiety.N-Heterocyclic ferrocenes coordinate to metal ions in monodentate, C,N-bidentate, multidentate, and bridging fashions, which results in metal complexes with various M:L stoichiometry. The ligands and their metal complexes have been recently employed for applications including chemical sensors, homogeneous catalysts, and redox-driven conformational switching.

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Reissert Compounds and Related N ‐Acyldihydroquinolines

Popp

1982

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Ferrocene studies. VI. Some heterocyclic derivatives of ferrocene

Cited by 11 publications

References 3 publications

Synthesis, crystal structures and electrochemistry of ferrocenyl-substituted 1,3,4-oxadiazoles

Synthesis, crystal structures and electrochemistry of ferrocenyl-substituted 1,3,4-oxadiazoles

Discrete metal complexes from N-heterocyclic ferrocenes: Structural diversity by ligand design

Reissert Compounds and Related N ‐Acyldihydroquinolines

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