The Condensation of Dicyclopentadienyliron with Aromatic Diazonium Salts

Weinmayr, Viktor

doi:10.1021/ja01616a027

Cited by 80 publications

(26 citation statements)

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“…4-Ferrocenylaniline can be synthesized by diazo-coupling of 4-nitrophenyldiazonium salt with ferrocene, followed by reduction [17,18], but we found that the use of Negishi coupling -coupling of ferrocenylzinc chloride with 4-iodoaniline in the presence of a palladium catalyst -was more convenient and resulted in a higher yield (29%) then the conventional method.…”

Section: Preparationmentioning

confidence: 91%

Synthesis and properties of azole-substituted ferrocenes

Mochida

Shimizu

Suzuki

et al. 2006

Journal of Organometallic Chemistry

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Section: Preparationmentioning

confidence: 91%

Synthesis and properties of azole-substituted ferrocenes

Mochida

Shimizu

Suzuki

et al. 2006

Journal of Organometallic Chemistry

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“…Reagent grade chemicals were employed in all cases. Ferrocene-Nphenylaza-15-crown-5 (1) was prepared by a literature procedure [26,27]. The structure of the compound has been previously characterized by elemental analysis, mass spectroscopy, and 1 H NMR spectroscopy [27].…”

Section: Methodsmentioning

confidence: 99%

Determination of the kinetic parameters of ferrocene-N-phenylaza-15-crown-5 by methods of convolution electrochemistry

Moharram

Ghoneim

2004

Journal of Electroanalytical Chemistry

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“…Various investigators have studied this reaction using aqueous acetic acid (19,69) or water-ether mixtures (13,70) as the reaction medium. Weinmayr has reported the successful arylation of ferricenium salts in aqueous sulphuric acid (71). The products of the arylation reactions are mono-, di-, and poly-arylferrocenes.…”

Section: Arylationmentioning

confidence: 99%

“…The deep blue, dichroic cation can readily be reduced t o ferrocene by means of reducing agents such as stannous chloride or ascorbic acid (71,115).…”

Section: Oxidation and Reductionmentioning

confidence: 99%

Metallocene Chemistry—a Decade of Progress

Rausch¹

1963

Can. J. Chem.

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One of the most significant new frontiers in chemistry during the past decade has been the stabilization and study of *-organic derivatives of the transition metals. Over 60 elements are now known to form one or more cyclopentadienyl compounds. The aromatic-type reactions displayed b y ferrocene and related complexes have also been extensively investigated. Ferrocene will undergo alkylation, acylation, sulphonation, metalation, arylation, formylation, aminomethylation, arid other reactions characteristic of a highly reactive aromatic system. H-Cyclopentadienyl derivatives of vanadium, chromium, manganese, ruthenium, and osmium as well as certain a-arene complexes of chromium exhibit ring substitution reactions in varying degrees. Other metallocenes undergo ring addition reactions.The orientation effects of substituents on reactions of substituted ferrocenes have been studied. A variety of unique oxidation, reduction, dehydration, and rearrangement reactions are known in metallocene chemistry. Haloferrocenes and mercuriferrocenes are readily converted to biferrocenyl. Recent rate investigations have established that carbonium ions adjacent to metallocene nuclei possess unusual stabilization as a result of direct metal participation.The chemistry of organometallic compounds has always intrigued chemists since the very beginning of this field over a century ago. Through the intervening years many outstanding discoveries have been made, and these discoveries have had a profound effect on t h e science of chemistry and chemical technology. In spite of extensive research in organometallic chemistry during the period from about 1830 to 1950, the preparation and study of organic derivatives of transition metals remained largely an enigma. The early work along these lines is well summarized in a recent review by Cotton (1).The accidental discovery of ferrocene in 1951 was a major event in organometallic chemistry. The isolation of this unique organo-iron compound has provided a tremendous stimulus for research leading t o many other types of novel organo-transition metal derivatives. Detailed studies on these derivatives in turn have contributed greatly to a better understanding of carbon -transition metal bonding.Certainly the most extensively investigated organo-transition metal complexes during the period from 1951 t o the present have been those in which the cyclopentadienyl group is present. Over 60 of the chemical elements have now been shown to form cyclopentadienyl derivatives. No doubt the ability of this group to form organometallic and organometalloidal compounds with so many elements results from the variety of ways it can enter into bonding. In a very broad sense cyclopentadienyl compounds of metals and metalloids can be classified according to whether the ring-metal bonding is principally ionic, principally covalent, or principally T-type. I t must be emphasized that these distinctions are not mutually exclusive, and that a given metal-cyclopentadienyl may possess bonding characteristics of several ...

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The Condensation of Dicyclopentadienyliron with Aromatic Diazonium Salts

Cited by 80 publications

References 0 publications

Synthesis and properties of azole-substituted ferrocenes

Synthesis and properties of azole-substituted ferrocenes

Determination of the kinetic parameters of ferrocene-N-phenylaza-15-crown-5 by methods of convolution electrochemistry

Metallocene Chemistry—a Decade of Progress

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