Oxidation of triphenylphosphine and norbornene by nitrous oxide in the presence of CoIILCl2 [L = 3-phenyl-5-(2-pyridylmethylidene)-2-thiohydantoin]: the first example of CoII-catalyzed alkene oxidation by N2O

Белоглазкина, Е. К.; Majouga, Alexander G.; Moiseeva, Anna A.; Зык, Н. В.; Зефиров, Н. С.

doi:10.1016/j.mencom.2009.03.005

Cited by 20 publications

(3 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Alternatively, the volatiles could be removed under reduced pressure and the residue purified by flash column chromatography (100% CH 2 Cl 2 followed by 100% CH 3 CN). Mp 481 K. 1 H NMR (DMSO-d 6 , 300 MHz) d 8.9 (d, 1H, J ¼ 8.0 Hz), 8.7 (d, 1H, J ¼ 4.5 Hz), 8.0 (t of d, 1H, J ¼ 7.8, 1.5 Hz), 7.6-7.3 (m, 6H), 6.9 (s, 1H), 2.7 (s, 3H).…”

Section: Methodsmentioning

confidence: 99%

“…The solid was collected by filtration to yield the product as a yellow solid in 93% yield. 1 H NMR (DMSO-d 6 , 300 MHz) d 11.9 (br s, 1H), 8.8 (d, 1H, J ¼ 4.8 Hz), 8.0 (t, 1H, J ¼ 8.3 Hz), 7.8 (d, 1H, J ¼ 8.0 Hz), 7.5 (m, 6H), 6.8 (s, 1H).…”

Section: Methodsmentioning

confidence: 99%

“…Recently, a cobalt complex bearing an easily prepared thiohydantoin ligand was reported to catalyze the oxidation of triphenylphosphine and the epoxidation of norbornene using N 2 O at RT. 1 Due to our interest in exploring thiohydantoins as tunable ligands for catalysts promoting olefin epoxidation using nitrous oxide as the terminal oxidant, we prepared 5-(pyridine-2-ylmethylene)-3-phenyl-2-methylthio-3,5dihydro-4H-imidazole-4-one (1, Fig. 1) for further study.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Polymorphism of 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-dihydro-4H-imidazole-4-one

et al. 2011

View full text Add to dashboard Cite

The title compound, C 16 H 13 N 3 OS (1), exists in three polymorphic forms. Crystalline 1 undergoes an enantiotropic, first-order, k2 phase transition at 262.9(5) K with DH ¼ 0.3(1) kJ mol À1 . Upon cooling below the transition temperature, the high temperature orthorhombic polymorph (Form I, space group Pbcm) transforms into a low temperature orthorhombic polymorph (Form II, space group Pbca) with a unit cell twice the size of that of the Form I. A molten 1 can be cooled in a controlled fashion to generate a monoclinic Form III of 1 with the unit cell size similar to that of Form I. Metastable Form III, once isolated, is indefinitely stable between 100 K and its melting point of 466 K. If crystals of Form III are in contact with seed crystals of Form I, a monotropic t2 first-order Form III / Form I phase transition occurs upon heating with the onset between 420 and 448 K and DH ¼ À1.7(4) kJ mol À1 . The most substantial differences among the molecular geometries of 1 in Forms I-III are observed in the position and tilt of the phenyl ring relative to the rest of the molecule. The packing in Form III is very different from those in the other polymorphs. DFT molecular geometry optimizations produce the following order of stable molecule configurations: Form II (most stable), Form I (0.50 kJ mol À1 ), Form III (2.81 kJ mol À1 ).

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Polymorphism of 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-dihydro-4H-imidazole-4-one

et al. 2011

View full text Add to dashboard Cite

show abstract

Synthese mit perfekter Atomökonomie: Erzeugung von Diazoketonen durch 1,3‐dipolare Cycloaddition von Distickstoffmonoxid an cyclische Alkine unter milden Bedingungen

Banert

Plefka

2011

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Zero‐Valent Amino‐Olefin Cobalt Complexes as Catalysts for Oxygen Atom Transfer Reactions from Nitrous Oxide

et al. 2016

View full text Add to dashboard Cite

The synthesis and characterization of several zerovalent cobalt complexes with ab is(olefin)-amino ligand is presented. Some of these complexes proved to be efficient catalysts for the selective oxidation of secondary and allylic phosphanes,a sw ell as diphosphanes,e ven with ad irect PÀP bond. With 5mol %c atalyst loadings the oxidations proceed under mild conditions (25-70 8 8C, 7-22 h, 2bar N 2 O) and affordg ood to excellent yields (65-98 %). In this process,t he greenhouse gas N 2 Oi sc atalytically converted into benign N 2 and added-value organophosphorus compounds,s ome of which are difficult to obtain otherwise.Phosphane oxides find applications mainly as:1 )l igands in metal-catalyzed cross-coupling reactions (secondary phosphane oxides,O = PHR 2 ), [1] 2) contact doping for silicon wafers and nanostructures, [2] 3) photoinitiators, [3] 4) constituents of phosphorescent organic light emitting diodes (the so-called PHOLEDs), [4] and 5) extracting agents for actinides,l anthanides and transuranic elements,toname afew. [5] Tr aditionally they are prepared from phosphanes by aerobic oxidation or treatment with peroxides.These methods can be cumbersome because of low selectivity and functional-group tolerance which may lead to complicated work-up protocols and/or generation of chemical waste.Additionally,these methods are not suitable for highly sensitive phosphanes containing C=C, -A (Venezuela) Dr.M .V ogt Current address:Institut fürAnorganische Chemie und Kristallographie, UniversitätB remen, LeobenerS tr.NW2, 28359 Bremen (Germany) Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

show abstract

Oxidation of triphenylphosphine and norbornene by nitrous oxide in the presence of CoIILCl2 [L = 3-phenyl-5-(2-pyridylmethylidene)-2-thiohydantoin]: the first example of CoII-catalyzed alkene oxidation by N2O

Cited by 20 publications

References 11 publications

Polymorphism of 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-dihydro-4H-imidazole-4-one

Polymorphism of 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-dihydro-4H-imidazole-4-one

Synthese mit perfekter Atomökonomie: Erzeugung von Diazoketonen durch 1,3‐dipolare Cycloaddition von Distickstoffmonoxid an cyclische Alkine unter milden Bedingungen

Zero‐Valent Amino‐Olefin Cobalt Complexes as Catalysts for Oxygen Atom Transfer Reactions from Nitrous Oxide

Contact Info

Product

Resources

About