Methyltrioxorhenium catalysed epoxidations: A comparative study of different N-donor ligands

Altmann, Philipp J.; Kühn, Fritz E.

doi:10.1016/j.jorganchem.2009.08.032

Cited by 21 publications

(8 citation statements)

References 36 publications

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“…The catalytic tests were performed at room temperature and twice with each ligand: once with exclusion of light and once in light with the goal to establish a statement about the supposed beneficial effect of chromophoric pyridine derivatives with respect to the already known advantages of simple pyridine derivatives in epoxidation catalysis with MTO. [19] Further details are given in the Exp. Section.…”

Section: Application In Epoxidation Catalysismentioning

confidence: 99%

“…This can be prevented by addition of bases, mostly pyridine, bipyridine or pyrazole and their derivatives, as shown by Sharpless et al and other groups. [8,[10][11][12][13][14][15][16][17][18][19] The photochemistry of MTO was for the first time under examination in the early 1990s. [20,21] MTO solutions were found to be very sensitive to UV light, the rhenium-carbon bond was reported to be photolysed after a short irradia-…”

Section: Introductionmentioning

confidence: 99%

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Chromophoric Lewis Base Adducts of Methyltrioxorhenium: Synthesis, Catalysis and Photochemistry

et al. 2010

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A series of chromophoric Lewis base adducts of methyltrioxorhenium (MTO) was examined. The ligands were pyridine derivatives with different size of the aromatic system and variable substituents, thus providing a variation of electronic and steric parameters. The complexes were fully characterised (UV/Vis, IR and NMR spectroscopy, single-crystal X-ray diffraction and elemental analysis) and their stability constants in dichloromethane were determined by means of UV/Vis spectroscopy. Moreover, this report presents a study of the influence of these N-donor ligands coordinated to MTO on the catalytic activity of epoxidation of 1-octene.

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Section: Application In Epoxidation Catalysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chromophoric Lewis Base Adducts of Methyltrioxorhenium: Synthesis, Catalysis and Photochemistry

et al. 2010

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“…50 % after 3 h (Figure 2). Interestingly, Schiff base 4 showed a much better performance than expected, based on previously published results 6b…”

Section: Resultsmentioning

confidence: 67%

Fluorinated Solvents in Methyltrioxorhenium‐Catalyzed Olefin Epoxidations

2012

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Epoxidations with methyltrioxorhenium(VII) (MTO) as catalyst precursor and additives are examined in fluorinated solvents under various conditions. These fluorinated solvents have a strong influence on the 1 H NMR, 13 C NMR, and 17 O NMR spectroscopic data of the catalyst precursor, apparently contributing significantly to the catalytic activity of such systems. Accordingly, the highest turnover frequencies (TOF) obtained with MTO-containing systems have been deter-[a] Chair

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“…The high TOFs were facilitated with excess pyrazole as the Schiff base additive and hexafluoroisopropanol (HFIP) as the solvent. Both the solvent and the Schiff base play important roles during the catalytic reaction as they are able to stabilize the catalytically active species, with the best yields for fluorinated solvents and nitrogen donor additives . This helps to enhance the yields and selectivities of the desired epoxides (Scheme ) .…”

Section: Methyltrioxorhenium and Related Compounds In Oxidation Catalmentioning

confidence: 99%

Molecular Epoxidation Reactions Catalyzed by Rhenium, Molybdenum, and Iron Complexes

Kück

Reich

Kühn

2016

The Chemical Record

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The reactions of a diborene with elemental selenium or tellurium are shown to afford a diboraselenirane or diboratellurirane, respectively. These reactions are reminiscent of the sequestration of sub-valent oxygen and nitrogen in the formation of oxiranes and aziridines; however, such reactivity is not known between alkenes and the heavy chalcogens. While carbon is too electronegative to affect the reduction of elements of lower relative electronegativity, the highly reducing nature of the B=B double bond enables reactions with Se 0 and Te 0. The capacity of multiple bonds between boron to donate electron density is highlighted in reactions where diborynes behave as nucleophiles, attacking one of the two Te atoms of diaryltellurides, forming salts consisting of diboratellurenium cations and aryltelluride anions.

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Methyltrioxorhenium catalysed epoxidations: A comparative study of different N-donor ligands

Cited by 21 publications

References 36 publications

Chromophoric Lewis Base Adducts of Methyltrioxorhenium: Synthesis, Catalysis and Photochemistry

Chromophoric Lewis Base Adducts of Methyltrioxorhenium: Synthesis, Catalysis and Photochemistry

Fluorinated Solvents in Methyltrioxorhenium‐Catalyzed Olefin Epoxidations

Molecular Epoxidation Reactions Catalyzed by Rhenium, Molybdenum, and Iron Complexes

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