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1

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O- und N-alkylsubstituierte 2-(2′-Hydroxyphenyl)-benzimidazole und -1,3,4-oxadiazole als Komplexbildner und Extraktionsmittel für Kupfer-II-ionen (1983)

Beger, J. ; Wagner, G. ; Uhlig, E. ; [et al.]

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 325 (1983), S. 708-718

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ISSN: 0021-8383

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: O- and N-Alkylsubstituted 2-(2′-Hydroxyphenyl)-benzimidazoles and -1,3,4-Oxadiazoles as Complexing and Extracting Agents for Copper-II-Ions2-(2′-Alkoxyphenyl)-benzimidazoles 1, 1-alkyl-2-(2′-hydroxyphenyl)-benzimidazoles 2, 2-(2′hydroxy-4′-alkoxyphenyl)-benzimidazoles 3, 2-(2′,4′-dialkoxyphenyl)-benzimidazoles 4 and 1-alkyl-2-(2′-hydroxy-5′-nitrophenyl)-benzimidazoles 7 are synthesized by condensation of 2-hydroxybenzoic acid derivatives and o-phenylenediamine or its derivatives. Alkyl chains C4, C8 or C12 are introduced by alkylation before or after the ring closure in order to increase the solubility of the reagent in toluene or n-octane. Furthermore the extraction properties of the benzimidazoles are investigated. Also some new analogous compounds of the benzothiazole and the 1,3,4-oxadiazole series were synthesized.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/prac.19833250505

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Komplexchemisches Verhalten von N-substituierten 2-(o—Hydroxyphenyl)-Δ2-imidazolinen als Metallextraktionsmittel (1983)

Beger, J. ; Wagner, G. ; Dinjus, U. ; [et al.]

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 325 (1983), S. 211-224

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ISSN: 0021-8383

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The Coordinative Behaviour of N-Substituted 2-(Δ2-Imidazolin-2-yl)-phenols as Metal ExtractantsN-Substituted 2-(Δ2-imidazolin-2-yl)-phenols (R4NNOH) are obtained by the reaction of N-alkyl diaminoethane-1, 2 and 2-hydroxybenzoic acid esters. In contrast to many other copper(II) complexes with the donor set N2O22-(A), the species Cu(R4NNO)2(B) are easily soluble in nonpolar solvents. The reason is the monomeric square-planar structure of B, which differs from the polymeric distorted octahedral structure of A.The two maxima in the vis-spectra of Cu(R4NNO)2 and Ni(R4NNO)2 are assigned to the 3 dxy → 3 dx2-y2 and the 3 dxz, 3 dyz → 3 dx2-y2 electron transitions. The shift of these maxima, which is connected with the dissolution in chloroform, is explained by the formation of hydrogen bonds between the solvent and the N-alkylated nitrogen atoms of the ligands.1H-n. m. r.-spectra and solubility of the ligands and the crystal structure of Cu[(C4H9)NNO]2 are described.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/prac.19833250206

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The electro-osmotic actuation of implantable insulin micropumps (1983)

Uhlig, E. L. P. ; Graydon, W. F. ; Zingg, W.

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 17 (1983), S. 931-943

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ISSN: 0021-9304

Keywords: Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: A study using an electro-osmotic cell suitable for actuating an implantable insulin micropump showed that controlled variable flow rates in the order of 0.2 mL/day are possible. The cell functioned continuously with low energy and power requirements and long service life. The principle of operation is compatible with achieving the very low flow rates necessary if highly concentrated insulin is to be used to avoid frequent insulin reservoir refilling. An electro-osmotic cell, Ag/ AgCl/NaCl(aq)/ cation exchange membrane/NaCl(aq)/ AgCl/ Ag, was connected to a constant current power supply which reversed the direction of the current every 10 mins causing a to-and-fro transport of fluid through the membrane. Flow rates of 0.15-0.60 μL/min were achieved with currents of 2.5-10 mA. At the low flow rate, energy consumption was 6.4 × 10-2 J/μL and peak power requirement was 〈2.0 × 10-4 W. Fluid was transported against a pressure gradient of 52 cm Hg. The cell contained a total electrolyte volume of 〈0.25 mL. The membrane showed no change in properties after 10,000 current reversals (69 days). To function as an actuator for an implantable insulin micropump, the electro-osmotic cell requires a switching and valving assembly; a suitable design for this is briefly considered.

Additional Material: 5 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jbm.820170605

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2-Bis(carboxymethyl)-amino-5-hydroxy-terephthalsäure als ambifunktioneller Ligand in Eisen(III)-Komplexen (1975)

Uhlig, E. ; Reif, D.

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 412 (1975), S. 227-238

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: 2-Bis(carboxymethyl)-amino-5-hydroxy-terephthalic Acid as an Ambifunctional Ligand in Iron(III) ComplexesFrom steric reasons the anthranilic acid -N,N-diacetic acid group and the salicylic acid group of 2-bis(carboxymethyl)-amino-5-hydroxy-terephthalic acid (H5C) cannot coordinate to the same central atom. With iron(III) H5C forms the mononuclear complex (HC)Fe(OH)2-, the central atom is fixed to the anthranilic acid N,N-diacetic acid group. In a weak acid medium (HC)Fe(OH)2- is converted into the binuclear species (HC)Fe(C)Fe(OH)4- which is of a deep red colour. In this complex the anion C5-has the function of a bridging ligand coordinating both by the anthranilic acid-N,N-diacetic acid group and by the salicylic acid group.The complex formation in the ternary system iron(III)/nitrilo triacetic acid/5-sulfo salicylic acid may be used as model for the dimerisation of the anion (HC)Fe(OH)2-.

Notes: In der 2-Bis(carboxymethyl)-amino-5-hydroxy-terephthalsäure H5C sind eine Anthranilsäure-N,N-diessigsäure- und eine Salicylsäure-Gruppierung räumlich so angeordnet, daß eine koordinative Wechselwirkung mit dem gleichen Zentralatom nicht möglich ist. Mit Eisen(III) bildet H5C den mononuklearen Komplex (HC)Fe(OH)2-, in dem das Zentralatom in der Anthranilsäure-N,N-diessigsäure-Gruppierung gebunden ist. (HC)Fe(OH)2- geht im schwach sauren Gebiet unter Wasserabspaltung in die binukleare Species (HC)Fe(C)Fe(OH)4- über. In diesem tiefrot gefärbten Komplex fungiert als- Anion C5- als Brückenligand und koordiniert sowohl über die Anthranilsäure- als auch über die Salicylsäure-Gruppierung.Die Dimerisierung des Anions (HC)Fe(OH)2- kann durch die Komplexbildung im ternären System Eisen(III)/Nitrilotriessigsäure/5-Sulfosalicylsäure modelliert werden.

Additional Material: 5 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19754120306

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Nickel(0)-Komplexe mit der zentralen Koordinationseinheit NiN2P2 (1976)

Dinjus, E. ; Gorski, I. ; Uhlig, E. ; [et al.]

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 422 (1976), S. 75-79

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: Nickel(0) Complexes with the Donor Set N2P2Mixed ligand complexes of the type (dipy)Ni(PR3)2 are stabil, provided the n-donor α,α′ -dipyridyl is combined with a tertiary phosphine or a phosphite acting as a π-acceptor. They may be prepared from (R3P)2Ni(C2H4) and dipy, from (dipy) Ni(COD) and PR3, or from (dipy) Ni(C2H5)2 and PR3. Starting with [(C6H11)3P]2Ni(C2H4) or (dipy)Ni(COD) the synthesis of the complex (dipy)Ni[P(C6H11)3]2 containing only n-donor ligands, failed. By the reaction of (dipy)Ni(C2H5)2 with (C6H11)3P the olefin complex [(C6H11)3P]2Ni(C2H4) was formed.

Notes: Gemischtliganden-Komplexe des Typs (dipy)Ni(PR3)2 sind dann stabil, wenn dem n-Donator α,α′-Dipyridyl ein Phosphan bzw. Phosphit mit π-Akzeptorfunktion als Zweitligand gegenübersteht. Sie können aus (R3P)2Ni(C2H4) und dipy, aus (dipy) Ni(COD) und PR3 oder aus (dipy)Ni(C2H5)2 und PR3 dargestellt werden.Die Synthese des Komplexes (dipy)Ni[P(C6H11)3]2, in dem nur n-Donatoren als Liganden vorlägen, gelang, wenn von [(C6H11)3P]2Ni(C2H4) oder (dipy)Ni(COD) ausgegangen wurde, nicht. Die Reaktion von (dipy) Ni(C2H5)2 mit (C6H11)3P führt zu [(C6H11)3P]2Ni(C2H4).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19764220110

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Triphenylphosphan-Komplexe des Nickel(O) mit Stickstoffheterocyclen als Zweitliganden (1975)

Uhlig, E. ; Dinjus, E.

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 418 (1975), S. 45-53

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: Triphenyl Phosphine Complexes of Nickel(O) Containing Nitrogen Heterocycles as Second LigandsThe mixed ligand complex (dipy)Ni(Ph3)2 is formed by the reaction of nickel(II) 1,3-diketonates, diethyl aluminium ethoxide, triphenyl phosphine, and α,α′-Dipyridyl or of (Ph3P)2Ni(C2H4) and α,α′-Dipyridyl. The second reaction is generally practicable and may be used to synthesize complexes of the types (Ph3P)2Ni(N∩N) (N∩N bidentate nitrogen ligand) and (Ph3P)2Ni(N∩P) (N∩P tertiary phosphane substituted by a pyridyl residue). In the case of the interaction with bulky N∩N-ligands both ethylene and triphenyl phosphine are substituted, and complexes of the type Ni(N∩N)2 are formed.Reaction mechanisms, 1H-nmr spectra and physical properties of the new complexes are discussed.

Notes: Der Gemischtligandkomplex (dipy)Ni(Ph3)2 entsteht im Zuge einer Eintopfreaktion aus Nickel(II)-1,3-diketonaten, Diäthylaluminiumäthoxid, Triphenylphosphan und α,α′-Dipyridyl oder aus (Ph3P)2Ni(C2H4) und α,α′-Dipyridyl. Die letztgenannte Reaktion ist verallgemeinerungsfähig und kann zur Synthese von Komplexen der Typen (Ph3P)2Ni(N∩N) (N∩N zweizähiger Stickstoffligand) und (Ph3P)2Ni(N∩P) (N∩P phosphansubstituiertes Pyridin) genutzt werden. Im Falle der Umsetzung mit voluminösen N∩N-Liganden werden sowohl Äthylen als auch Triphenylphosphan substituiert, und es entstehen Komplexe des Typs Ni(N∩N)2.Bildungsmechanismus, 1H-NMR-Spektren und physikalische Eigenschaften der neu dargestellten Komplexe werden diskutiert.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19754180106

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Zum Einfluß der Ringgröße auf die Struktur von Metallchelaten. IV. Palladium(II)- und Platin(II)-Komplexe pyridylsubstituierter Dialkylsulfide und -amine (1977)

Uhlig, E. ; Borek, B. ; Ngu, Le My

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 432 (1977), S. 33-41

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: The Influence of Ring Size on the Structure of Metal Chelates with Tridentate Ligands. IV. Palladium(II) and Platinum(II) Complexes of Pyridyl Substituted Dialkyl Sulfides and Amines[β-(Pyridyl-2)-ethyl]-[(pyridyl-2)-methyl]-amine(2,3-py2tri) forms planar palladium(II) complexes [Pd(2,3-py2tri)X]X (X = Cl, Br) occupying trans-positions as a tridentate ligand. An analogous behaviour is observed with bis[β-(pyridyl-2)-ethyl]-sulfide(3,3-py2Stri) in the chelate compounds [MeII(3,3-py2Stri)X]X (MeII = Pd, Pt; X = Cl, Br, J, SCN). On the other hand the rigid ligand bis[(pyridyl-2)-methyl]-sulfide(2,2-py2Stri) is only bidentate in the complexes MeII(2,2-py2Stri)X2 (MeII = Pd, Pt; X = Cl, Br, J, SCN), one pyridine group does not interact with the central atom. The reasons are the angular relations within the thioether group of 2,2-py2Stri which allow a tridentate coordination in a facial conformation (octahedral and trigonal-bipyramidal nickel(II) and copper(II) complexes), but not in a meridional one (planar palladium(II) and platinum(II) complexes).In Pt(2,2-py2Stri)(SCN)(NCS) one thiocyanato ligand is linked by sulfur, the other one by nitrogen.

Notes: [β-(Pyridyl-2)-äthyl]-[(pyridyl-2)-methyl]-amin(2,3-py2tri) bildet planare Palladium(II)-Komplexe [Pd(2,3-py2tri)X]X (X = Cl, Br), in denen es als dreizähliger Ligand Trans-Positionen überspannt. Ganz analog verhält sich Bis[β-(pyridyl-2)-äthyl]-sulfid(3,3-py2Stri) in den Chelatverbindungen [MeII(3,3-py2Stri)X]X (MeII = Pd, Pt; X = Cl, Br, J, NCS). Dagegen besetzt der starre Ligand Bis-[(pyridyl-2)-methyl]-sulfid(2,2-py2Stri) in den Komplexen MeII(2,2-py2Stri)X2 (MeII = Pd, Pt; X = Cl, Br, J, SCN) nur zwei Koordinationsstellen, ein Pyridinhaftatom geht keine Wechselwirkung mit dem Zentralatom ein. Der Grund dafür wird in den Winkelverhältnissen der Thioäthergruppierung von 2,2-py2Stri gesehen, die eine dreifache Koordination nur bei facialer Anordnung (oktaedrische und trigonal-bipyramidale Nickel(II)- und Kupfer(II)-Komplexe), nicht aber bei meridionaler (planare Palladium(II)- und Platin(II)-Komplexe) ermöglicht.Im Pt(2,2-py2Stri)(SCN)(NCS) ist ein Thiocyanatoligand über den Schwefel, der andere über den Stickstoff gebunden.

Additional Material: 2 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19774320104

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Substitutionsreaktionen mit Gemischtligand-Komplexen des Nickel(0). I. Reaktionen mit Heteroolefinen (1977)

Dinjus, E. ; Gorski, I. ; Matschiner, H. ; [et al.]

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 436 (1977), S. 39-46

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: Substitution Reactions with Mixed Ligand Complexes of Nickel(0). I. Reactions with HeteroolefinesThe mixed ligand complexes (C2H4)Ni(PPh3)2 (A) and (COD) Ni(dipy) (B) react with “heteromonoolefines” L (carbonyl compounds, azomethines, azobenzene) by substitution forming LnNi(PPh3)2 or LnNi(dipy). In these complexes the heteromonoolefines are coordinated side-on as π-acid ligands. α-β-unsaturated carbonyl compounds, which are bonded by the C=C and not by the C=O function, take a special position.The olefines of A and B may also be substituted by diheterodiolefines L′(1,2-diketones and the corresponding diimines). However in the case of the reaction with the diimines not only compounds like L′Ni(PPh3)2 or L′Ni(dipy) but also bischelates like NiL′2 are easily formed by a further substitution.For the course of the substitution reactions the energy of the π*-orbital of the heteroolefine, which may be expressed by the polarographic half wave potential, is of a high importance. Heteroolefines with E1/2 〈 -2000 mV (acetone, ethyl benzoate) either do not react with the mixed ligand complexes A and B or the substitution requires special conditions (propanal). Relations and differences of B and (dipy)NiEt2 as to their reactivities with heteroolefines are discussed.

Notes: Die Gemischtligand-Komplexe (C2H4)Ni(PPh3)2 (A) bzw. (COD) Ni(dipy) (B) reagieren mit “Heteromonoolefinen” L (Carbonylverbindungen, Azomethine, Azobenzol) unter Substitution zu LnNi(PPh3)2 bzw. LnNi(dipy). Die Heteromonoolefine koordinieren in diesen Komplexen “side-on” als π-Säure-Liganden. Eine Sonderstellung nehmen α, β-ungesättigte Carbonyl-verbindungen (Acrolein, Dibenzylidenaceton) ein, die nicht über die C=O-, sondern über die C=C-Gruppierung gebunden werden.Die Olefine in A und B können auch durch Diheterodiolefine (1,2-Diketone und die zugehörigen Diimine) substituiert werden (Bildung von L′Ni(PPh3)2 bzw. L′Ni(dipy)). Im Falle der Umsetzung mit den Diiminen entstehen jedoch leicht durch weitere Substitution die vierfach-koordinativen Bischelate NiL′2.Für den Ablauf der Substitutionsreaktionen ist die Lage des π*-Orbitals der Heteroolefine von Bedeutung, die im polarographischen Halbstufenpotential ihren Ausdruck findet. Heteroolefine mit E1/2 〈 -2000 mV (Aceton, Benzoesäureäthylester) reagieren nicht mit den betrachteten Gemischtligandkomplexen oder nur unter verschärften Bedingungen (Propionaldehyd). Es werden Analogien und Unterschiede in der Reaktivität von B bzw. (dipy)NiEt2 gegenüber Heteroolefinen diskutiert.

Additional Material: 2 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19774360104

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Substituierte 2-(Thiazol-4-yl)-phenole als Liganden und potentielle Extraktionsmittel für Kupfer(II)Professor Günther Schott zum 60. Geburtstage am 29. April 1981 gewidmet (1981)

Dinjus, U. ; Uhlig, E. ; Beger, J. ; [et al.]

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 476 (1981), S. 16-22

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: Substituted 2-(Thiazol-4-yl)-phenols as Ligands and Potential Extractants for Copper (II)Substituted 2-(thiazol-4-yl)-phenols are obtained by the HANTZSCH synthesis. Their solubility in toluene is higher than in n-octane depending on the position, the chain length, and the polarity of the substituents. From alcoholic solutions complexes of the type CuL2n are precipitated. According to the substituents their structure is distorted octahedral (CuL22, CuL23) or distorted tetrahedral (CuL28, CuL29). The new complexes are nearly insoluble in toluene and aliphatic hydrocarbons, but CuL28 and CuL29 are soluble in chloroform. Therefore copper(II) may be extracted by HL8 and HL9 using chloroform as a diluent.

Notes: Durch die HANTZSCHsche Synthese werden substituierte 2-(Thiazol-4-yl)-phenole HLn hergestellt. Ihre Löslichkeit ist in Toluen besser als in n-Octan und hängt von der Stellung, der Kettenlänge und der Polarität der Substituenten ab. Aus alkoholischen Lösungen kristallisieren Komplexe des Typs CuL2n. Je nach den Substituenten ist ihre Struktur verzerrt oktaedrisch (CuL22, CuL23) oder verzerrt tetraedrisch (CuL28, CuL29). Alle neu dargestellten Kupfer(II)-Komplexe sind in Toluen und aliphatischen Kohlenwasserstoffen schwer löslich. Dagegen lösen sich die Verbindungen CuL28 und CuL29 gut in Chloroform. Kupfer(II) kann daher mit HL8 und HL9 in Chloroform als Verdünnungsmittel extrahiert werden.

Additional Material: 4 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19814760503

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Zur Oxydation von Gemischtligand-Nickel(0)-Komplexen mit organischen Halogeniden (1981)

Uhlig, E. ; Poppitz, W.

Weinheim : Wiley-Blackwell

Zeitschrift für anorganische Chemie 477 (1981), S. 167-177

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ISSN: 0044-2313

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: Oxidation of Mixed Ligand Nickel(0) Complexes by Organic HalidesThe oxidation of (dipy)Ni(PPh3)2 by alkyl and aryl iodides or bromides affords the nickel(I) complexes (dipy)Ni(PPh3)X (X = Br, I). No normal products of oxidative addition are obtained. But in the case of methyl and ethyl halides complexes of the type (dipy)NiR2 are formed as intermediates. Basing on the identified final products and on the correalation between the reactivity of the organic halides and their polarographic half wave potentials a mechanism of the reaction is proposed. The first step is a charge transfer from nickel(0) to the organic halide.Further synthesis, reactions, and the ESR-spectra of the complexes (dipy)Ni(PPh3)X and a synthesis of (dipy)Ni(CH2Ph)2 are described. Experiments to prepare pure (dipy)Ni(PPh3)Cl had no success.

Notes: (dipy)Ni(PPh3)2 wird von Alkyl- und Aryliodiden bzw. -bromiden zu den Nickel(I)-Verbindungen (dipy Ni(PPh3)X (X = I, Br) oxydiert. Normale Produkte der oxidativen Addition werden nicht gefunden. Im Falle der Methyl- bzw. Ethylhalogenide entstehen jedoch Komplexe des Typs dipy)NiR2 als Intermediate. Auf Grund der identifizierten Endprodukte und der Zusammenhänge zwischen der Reaktivität der organischen Halogenide und ihrer polarographischen Halbstufenpotentiale wird ein Reaktionsmechanismus vorgeschlagen, an dessen Anfang ein Chargetransfer vom Nickel(0)-Komplex zum organischen Halogenid steht.Es werden weitere Synthesemöglichkeiten, Reaktionen und die ESR-Spektren der Komplexe (dipy)Ni(PPh3)X sowie die Synthese von (dipy)Ni(CH2Ph)2 mitgeteilt. Die Darstellung von reinem (dipy)Ni(PPh3)Cl gelang nicht.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/zaac.19814770623

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