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1

Efficient Catalytic Systems for Synthesis of 5,5''-Dibromo-2,2':6',2''-terpyridine and 5,5'-Dibromo-2,2'-bipyridine via Coupling of Dihalogenopyridines with 5-Bromo-2-trialkylstannylpyridines

Krompiec S., Ignasiak H., Krompiec M., Stanek Ł., Filapek M., Gębarowska K., Penczek R.

Polish Journal of Chemistry

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2009

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Vol. 83, nr 2

245-262

EN

The results of the studies on the synthesis of 5,5'-dibromo-2,2'-bipyridine and 5,5''-dibromo-2,2':6',2''-terpyridine via coupling of 5-bromo-2-iodopyridine and 2,6-dihalogenopyridines with 5-bromo-2-trialkylstannylpyridines mediated by palladium catalysts have been presented. The catalytic activity of the Pd(II) and Pd(0) complexes (e.g. [PdCl2(PPh3)2], [PdCl2(COD)], [Pd(dba)2]), and catalytic systems generated in situ from a stable precursor (e.g. [PdCl2], [Pd(acac)2]) and an external ligand (APh3, where A = P, As, Sb; phosphines, phosphites) in the coupling of diiodopyridine with 5-bromo-2-tributylstannylpyridine was investigated. The most active system was that generated from [Pd(acac)2] and P(OPh)3, while the highest coupling selectivity was achieved with [Pd(acac)2] and PPh3. The catalytic activity of systems containing chelating ligands BINAP or dppf was slightly inferior. In all reactions the formation of 5,5'-dibromo- 2,2'-bipyridine, the product of homocoupling of 5-bromo-2-tributylstannylpyridine, was observed. An increase of the L/Pd ratio for catalytic system generated from [Pd(acac)2] and P(OPh)3 resulted in improved selectivity of dbtpy formation (the yield of dbbpy, the product of homocoupling, decreased) and in an increased stability of the catalytic system (without decreasing the reaction rate even for Pd/L = 1:32). On the other hand, for the systems containing phosphines the increase of L/Pd above 4:1 for monodentate phosphines and above 2:1 forbidentate phosphines resulted in a fast decrease of the reaction rate. The coupling is faster for 2,6-diiodopyridine and slower for 2,6-dibromo pyridine, while 2,6-dichloropyridine is nonreactive. The yield of coupling for trimethyl- and tributylstannyl derivatives is practically identical. Particularly advantageous solvents for the studied coupling reaction are xylene, toluene, and 1,2-diethoxyethane.

2

Reakcje kompleksów di-ž-chlorobis[(N-t-butylofor-mimidoilo)-4R-fenylo-2C,N-dipalladów z podstawionymi terminalnymi alkenami

Majewski J., Krompiec S.

Chemik

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2005

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Vol. 58, nr 6

365-366

PL

Zsyntezowano metaloorganiczne kompleksy palladu(II) w reakcji chlor-ku palladu(II) z N-(4-R-benzylideno)-t-butyloaminą, otrzymując di-m-chlo-ro-bis[(N-t-butyloformimidoilo)-4-R-fenylo-2C,N]dipallady(II), gdzie R = H, OCH3. Kompleksy te poddano reakcji z funkcyjnie podstawionymi, terminalnymi alkenami: akrylanem metylu i akrylonitrylem, otrzymując z dobrymi wydajnościami orto dipodstawione pochodne winylowe, a w przypadku reakcji z akrylonitrylem pochodne izochinoliny.

EN

Metaloorganic complexes of palladium (II) were synthesised in the reaction of palladium(II) chloride with N-(4-R-benzylidene)-t-butylamine, where the suitable di-ž-chlorobis[(N-t-butyloformimidoyl)-4-R-phenyl-2C,N]di-palladiums(II) were obtained (R=H, OCH3). These complexes react with the substituted terminal alkenes, such as: methyl acrylate and acrylonitryle, giving orto disubstituted vinyl derivatives with a good yield, and in the case of the reaction with acrylonitryle - isoquinoline derivatives.

3

Synteza monomerów 0-(1-propenylowych) przez katalizowaną kompleklsami rutenu izomerację odpowiednich układów allilowych

Urbala M., Kuźnik N., Krompiec S., Antoszczyszyn M., Martysz D.

Przemysł Chemiczny

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2003

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T. 82, nr 8-9

642-644

4

Non-waste synthesis of 1-propenoxyl monomers

Urbala M., Antoszczyszyn M., Krompiec S.

Polish Journal of Chemical Technology

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2001

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Vol. 3, nr 3

22-24

EN

Non-waste synthesis of 1-propenoxyl monomers of C4 diols ((Z)-butane-2-ene-l,4-diols) via isomerization of the corresponding allyl ethers of diols catalysed by the ruthenium(II) complexes has been investigated. [RuHCl(CO)(PPh3)3] is a very active and selective catalyst precursor of isomerization of allyl ethers of diols, containing neither a triple bond nor unprotected primary allylic hydroxyl group. The optimal parameters for the synthesis of 1-propenyl ethers and their physic-chemical properties ('H NMR, MS, boiling point) are given. Synthesized propenyl ether monomers were of high purity, therefore, they are suitable directly for use in photointiated cationic polymerization.

5

Badanie właściwości termicznych wybranych organicznych kompleksów rutenu i palladu

Matysek-Majewska D., Majewski J., Krompiec S.

Zeszyty Naukowe. Chemia / Politechnika Śląska

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2000

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z. 141

13-19

PL

Wykonano badania derywatograficzne wybranych, organicznych kompleksów rutenu i palladu, posiadających ligandy zawierające atomy fosforu i azotu. Kompleksy te znajdują zastosowanie w syntezie organicznej jako katalizatory w reakcji winylowania i izomeryzacji. Określona została termiczna trwałość kompleksów, charakter zachodzących przemian oraz wielkości efektów energetycznych, towarzyszących przemianom.

EN

The derivatographic investigations of chosen organic complexes of ruthenium and palladium, containing ligands with phosphorus and nitrogen atoms have been carried out. These complexes are applied as catalysts in the vinylation and isomerisation reactions. Thermal stability of complexes, kind of transformation and their energetic effects were established.

6

Zastosowanie organizacji połączeń tytanu i krzemu w technologii krzemowej

Krompiec S., Majewski J., Matysek-Majewska D., Waczyński K.

Zeszyty Naukowe. Chemia / Politechnika Śląska

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1998

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z. 137

227-234

PL

Przedstawiono badania z zastosowaniem organicznych kompleksów tytanu oraz wybranych związków fosforu, boru, arsenu i antymonu do modyfikacji powierzchni płytek krzemowych, stosowanych w elektronice. Z szeregu przetestowanych kompleksów tytanu najlepsze właściwości dla otrzymania antyrefleksyjnych powłok tlenku tytanu (IV) wykazał diizopropoxy-bis(2,4-pentanodioniano)tytan(IV). Do wytwarzania szkliw domieszkowych wytypowano tetraetoksysilan, kwas borowy(III), kwas fosforowy(V), chlorek antymonu(III) i kwas arsenowy(V).

EN

The investigations on the application of complexes of titanium and selected phosphorus, boron, arsenic and antimony compounds for the modification of the obtaining thesurface of silicone plates for electronic purposes have been presented. The best properties for obtaining the titanium dioxide antireflective coatings performs, among number of examined titanium complexes, diizopropoxobis(2,4-pentanedionato)titanium. Tetraethoxysilane, boric acidphosphoric acid, antimonium (III) chloride and arsenic acid were chosen for the preparation of doping glazes.

7

Isomerization of vegetable oils catalyzed by ruthenium complexes

Krompiec S., Suwiński J., Majewski J., Grobelny J.

Polish Journal of Applied Chemistry

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1998

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Vol. 42, nr 1

43-48

EN

A study on isomerization of industrial oils - rapeseed, soybean, suntlower and linseed - was performed in the presence of the following ruthenium complexes: [RuHCl (CO)(PPh(3), [Ru(CO)3(PPh(3)2], [Ru(C2(1,5-COD)]x [Ru(acac)3], [RuCl2(PPh3)3)3], (RuH2(PPh3)]4], [RuCl2(AsPh3]3], [RuCl2(NBD)]x and [RuCl2(SbPh3)3]. The reactions were carried out in bulk under air atmosphere at 212st.C and 226st.C. Concentration of the complexes corresponded to 58 or 116 ppm of ruthenium. The best results were obtained with [RuHCl(CO)(PPh3)3 as the catalyst. Separation of the catalyst from isomerized oils was accomplished by sorption on diatomaceous earth or on active carbon. The isomerized rapeseed, soybean, sunllower and linseed oils were found to contain respectively 30, 54, 54 and 50 wt-% of conjugated isomers, up to 10 wt-% of polymeric materials and less than 1 ppm of ruthenium.