FERROCENE BRIDGING AND HOMOANNULAR CYCLIZATIONS<sup>1</sup>

Rinehart, Kenneth L.; Curby, Ronald J.

doi:10.1021/ja01569a084

Cited by 67 publications

(47 citation statements)

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“…OF THE TRICLINIC MODIFICATION OF QUINHYDRONE The stable bridged 'sandwich' compound ~-keto-l,l'-trimethyleneferrocene, C13H12OFe (I), may be prepared by the procedure of Rinehart & Curby (1957).…”

Section: Structurementioning

confidence: 99%

The crystal structure of α-keto-1,1'-trimethyleneferrocene

Jones¹,

Marsh²,

Richards³

1965

Acta Crystallogr

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Section: Structurementioning

confidence: 99%

The crystal structure of α-keto-1,1'-trimethyleneferrocene

Jones¹,

Marsh²,

Richards³

1965

Acta Crystallogr

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“…1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (EDC; Acros Organics), HOBt (Aldrich) and di-t-butyldicarbonate (Acros Organics) were used as received. The syntheses of carbohydrate 11 [23] and organometallic starting materials 1 and 2 [25,26] were performed according to literature data. Products were purified by preparative TLC on silica gel (Merck, Kieselgel 60 HF 254 ).…”

Section: Experimental Materials and Methodsmentioning

confidence: 99%

“…[25,26] Keto-acids 1 (6 g, 21 mmol) and 2 (6 g, 20 mmol) were suspended in cold AcOH (80 ml) and conc. hydrochloric acid (120 ml), respectively, then cooled in an ice bath and stirred vigorously during addition of small portions of Zn-amalgam (30 g) over a period of 45 min.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, spectral characterization and inhibitory potency of ferrocene‐containing mannosides towards type 1 fimbriated Escherichia coli

Kovač

Ribić

Peroković

et al. 2016

Applied Organom Chemis

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Escherichia coli adhesion to the bladder epithelium is mediated through recognition of the tissue-surface mannosylated proteins with bacterial lectin FimH. The inhibition of this recognition-dependent interaction has been recognized as a promising strategy for the development of an anti-adhesion therapy. Mannosides with either aryl-or elongated alkyl-functionalized aglycon portions have been shown to be potent inhibitors of FimH-mediated adhesion. Thus, we have synthesized four mannose-based bioorganometallics containing an extended alkyl chain between sugar and ferrocene components connected via ester linkage (14 (n = 4) and 15 (n = 5)) or amide linkage (18 (n = 3) and 19 (n = 4)). The novel bioconjugates were characterized using infrared and NMR ( 1 H, 13 C, COSY, NOESY, HSQC, HMBC) spectroscopies, electrospray ionization mass spectrometry and high-resolution mass spectrometry. Hemagglutination inhibitory assay of the novel bioorganometallics revealed an enhanced inhibitory potential in comparison to methyl α-D-mannoside. Thereby, the bioconjugate 19 exhibited a twofold increase in inhibitory activity compared with 14, 15 and 18.

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“…Thin-film chromatography indicated a faint amount of a byproduct, possibly the Nb + dye. The ferrocenophane (Fcp) was synthesized according to ref 43 and characterized by NMR and CHN analysis. Nile blue (Nb + ) chloride was used as received from Sigma Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Magnetic Field and Temperature Dependencies Shed Light on the Recombination Kinetics of a Transition Metal Donor/Acceptor System

et al. 2005

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Abstract:The radical pair recombination of an intramolecular electron-transfer system containing a transition metal moiety has been addressed by femtosecond spectroscopy. The radical pair is formed by ultrafast electron transfer (90 fs) from a ferrocene residue to a photoexcited Nile blue moiety. Its recombination proceeds on the picosecond time scale in a multiexponential fashion. The kinetic pattern is a manifestation of spin processes competing with electron transfer. Magnetic field effects on these kinetics allow one to disentangle the two contr butions. Their temperature dependencies yield the activation parameters of the two processes. The discussion focuses on the mechanism of electron spin relaxation. Strong evidence for the Orbach/Kivelson mechanism will be given.

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FERROCENE BRIDGING AND HOMOANNULAR CYCLIZATIONS¹

Cited by 67 publications

References 0 publications

The crystal structure of α-keto-1,1'-trimethyleneferrocene

The crystal structure of α-keto-1,1'-trimethyleneferrocene

Synthesis, spectral characterization and inhibitory potency of ferrocene‐containing mannosides towards type 1 fimbriated Escherichia coli

Magnetic Field and Temperature Dependencies Shed Light on the Recombination Kinetics of a Transition Metal Donor/Acceptor System

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FERROCENE BRIDGING AND HOMOANNULAR CYCLIZATIONS1

Cited by 67 publications

References 0 publications

The crystal structure of α-keto-1,1'-trimethyleneferrocene

The crystal structure of α-keto-1,1'-trimethyleneferrocene

Synthesis, spectral characterization and inhibitory potency of ferrocene‐containing mannosides towards type 1 fimbriated Escherichia coli

Magnetic Field and Temperature Dependencies Shed Light on the Recombination Kinetics of a Transition Metal Donor/Acceptor System

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FERROCENE BRIDGING AND HOMOANNULAR CYCLIZATIONS¹