Studies on ferrocene derivatives. Part 12. Substituent effects for the disproportionation, synproportionation and ligand exchange reactions of t-butylferrocenes

Hayashi, Takatoshi; Okada, Yutaka; Shimizu, Satoshi

doi:10.1007/bf00140783

Cited by 8 publications

(5 citation statements)

References 7 publications

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“…The yield of the ligand exchange product for thiophene was 3.1% -4.8%, which was much lower than that of the hydrocarbon mentioned in previous papers [7] [8]. These results are supported by the fact that the product from thiophene shows lower chemical shifts of the Cp ring than that of the other products ( Table 6).…”

Section: The Ligand Exchange Reaction With Five-membered Heterocyclessupporting

confidence: 53%

Ligand Exchange Reaction of Ferrocene with Heterocycles

Okada¹,

Huruya²,

Imori³

2015

IJOC

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The ligand exchange reaction with heterocycles containing nitrogen, oxygen or sulfur atoms was carried out. For the reaction with heterocycles, the order of the reactivity was S-heterocycles > N-heterocycles > O-heterocycles. Furthermore, when the results for the heterocycles were compared to those for the corresponding hydrocarbons, the hydrocarbons had a higher reactivity. These results mean that the reactivity would be mainly governed by the electron density of these arenes.

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Section: The Ligand Exchange Reaction With Five-membered Heterocyclessupporting

confidence: 53%

Ligand Exchange Reaction of Ferrocene with Heterocycles

Okada¹,

Huruya²,

Imori³

2015

IJOC

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“…With respect to the second ligand transfer, that of the Cp ring from iron to rhenium, there is considerable literature precedent for AlCl 3 -induced Fe−Cp bond breakage but these reactions generally involve Cp ring replacement by an arene (e.g. benzene) − or ring interchange between differentially substituted ferrocene molecules. − Outside of the DLT reaction, the only example of Cp ring transfer from ferrocene to another metal is the reaction of ferrocene with RuCl 3 to produce ruthenocene. , …”

Section: Discussionmentioning

confidence: 99%

“…benzene) [31][32][33] or ring interchange between differentially substituted ferrocene molecules. [34][35][36][37][38] Outside of the DLT reaction, the only example of Cp ring transfer from ferrocene to another metal is the reaction of ferrocene with RuCl 3 to produce ruthenocene. 24,25 The family of reactions that are perhaps most similar to the DLT are those involving Cp ring transfer to various metals from [CpFe(CO) 2 ] 2 or CpFe(CO) 2 Br.…”

Section: Discussionmentioning

confidence: 99%

Preparation of Cyclopentadienyltricarbonylrhenium Complexes Using a Double Ligand-Transfer Reaction

Spradau

Katzenellenbogen

1998

Organometallics

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A unique double ligand-transfer reaction is described for the preparation of substituted cyclopentadienyltricarbonylrhenium complexes. In the reaction, potassium perrhenate(VII) is reduced and carbonylated by treatment with chromium trichloride and chromium hexacarbonyl to provide a proposed alkoxy carbonyl rhenium(I) intermediate. It is believed that this intermediate then undergoes a Cp ligand-transfer reaction with an acyl-substituted ferrocene to provide the corresponding (acyl-cyclopentadienyl)tricarbonylrhenium complex. A strongly coordinating solvent such as methanol is necessary to promote the reduction of perrhenate, and a carbonyl substituent conjugated to the Cp ring is necessary to activate it for transfer from iron to rhenium. This method has potential value for the synthesis of rhenium and technetium organometallic radiopharmaceuticals.

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“…[34,35] We have previously discussed the preparation and properties of Cp-methylated PFSs. [27] We thus undertook a preliminary study to test the durability of such materials in the photooxidation with CHCl 3 and reduction with Cp 2 *Fe process, using the same conditions applied to the PFMPS films.…”

Section: Reduction Of Photooxidized Pfmpsmentioning

confidence: 99%

Photooxidation and Photoconductivity of Polyferrocenylsilane Thin Films

Cyr¹,

Tzolov²,

Manners³

et al. 2003

Macro Chemistry & Physics

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Irradiation of thin films of poly(ferrocenylmethylphenylsilane) ([Fe(η5‐C5H4)2SiMePh]n) cast from chloroform solution with UV light leads to photooxidation of ferrocene centers in the polymer main chain. The extent of the polymer oxidation can be controlled in the range ca. 0–5% by the duration of the irradiation exposure and by the concentration of chloroform. The photooxidized polyferrocenylsilane material is conductive, with an increased conductivity of greater than three orders of magnitude relative to the unoxidized material. In addition, the photooxidized polymers have been found to be photoconductive. The photooxidation process can be reversed by means of chemical reduction using hydrazine or decamethylferrocene, leading to the regeneration of the neutral polymers. However, substantial molecular weight decline was detected during the photooxidation/reduction process, presumably as a result of chain cleavage reactions induced by the anionic or radical chlorinated photoproducts. Methylation of the cyclopentadienyl rings of the ferrocene moiety in the polymer was found to lead to materials which are significantly more stable.Time trace of the current at constant applied voltage of 100 V for a PFS film upon illumination. The ON and OFF states were created by using a mechanical shutter.magnified imageTime trace of the current at constant applied voltage of 100 V for a PFS film upon illumination. The ON and OFF states were created by using a mechanical shutter.

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Studies on ferrocene derivatives. Part 12. Substituent effects for the disproportionation, synproportionation and ligand exchange reactions of t-butylferrocenes

Cited by 8 publications

References 7 publications

Ligand Exchange Reaction of Ferrocene with Heterocycles

Ligand Exchange Reaction of Ferrocene with Heterocycles

Preparation of Cyclopentadienyltricarbonylrhenium Complexes Using a Double Ligand-Transfer Reaction

Photooxidation and Photoconductivity of Polyferrocenylsilane Thin Films

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