Dieter Guhl - Academia.edu (original) (raw)
Papers by Dieter Guhl
ChemInform, Mar 6, 1990
ChemInform Abstract The fluorine-substituted alkenes (I) undergo highly regioselective 1:1 CC-cou... more ChemInform Abstract The fluorine-substituted alkenes (I) undergo highly regioselective 1:1 CC-coupling with phenylisocyanate (II) on Ni0 systems to form the azanickelacyclopentanones (V). As shown by NMR, the coordination geometry about nickel is approximately square planar. The reactivity of these complexes differs strongly from that of known alkyl-or arylsubstituted nickela-systems, as shown by the behavior of (V) during hydrolysis, thermolysis or reaction with electrophiles.
ChemInform, 1989
ChemInform Abstract The catalytic addition of isocyanates to CC double or triple bond compounds i... more ChemInform Abstract The catalytic addition of isocyanates to CC double or triple bond compounds is running via aza-nickela-heterocyclic intermediates of type (V) and (VI). When vinylcyclohexane (I) reacts with phenyl isocyanate (II) in the presence of Ni(cod)2 and the ligand tricyclohexylphosphane, anilides (III) and (IV) are obtained (no yields given). However, intermediates of type (V) are sometimes able to abstract intramolecularly a β-H, thus producing unsaturated products and reforming the catalyst. To test, if β-H abstraction is possible not only from the heterocyclic ring but from an exocyclic position as well, the reaction is also conducted according to A), B) or C) and indeed, depending on the ligand, the reaction is directed towards an equal abstraction from both β-positions or to a nearly unique preference of one of the two β-positions.
Synthesis and Application of Metal Methansulphonic Acid salts
Journal of Organometallic Chemistry, 1989
ABSTRACT The use of chelating ligands such as DCPE, BIPY and TMEDA as stabilizing ligands permits... more ABSTRACT The use of chelating ligands such as DCPE, BIPY and TMEDA as stabilizing ligands permits the preparation of the novel ligand-Ni complexes of 1,1-difluoroethene. The structures of the 16e complexes were confirmed by 1H, 13C, 19F and 31P NMR spectroscopy. Characteristic properties are described.
Journal of Organometallic Chemistry, 1990
ABSTRACT 1,7-Octadiene and phenylisocyanate react with the (Lig)Ni0-system, depending on the liga... more ABSTRACT 1,7-Octadiene and phenylisocyanate react with the (Lig)Ni0-system, depending on the ligand, to give differing products. Thus with tricyclohexylphosphane the reaction is accompanied by cyclization and (2-methylenecyclohexyl)acetanilide(V) is formed. On the other hand, reaction with the weakly basic tricyclohexylphosphite gives the acyclic nona-2,8-dienecarboxanilide (VI).
Journal of Organometallic Chemistry, 1988
ABSTRACT Isocyanates react with propene at ligand-nickel(0) systems by 1/1 CC coupling to give tw... more ABSTRACT Isocyanates react with propene at ligand-nickel(0) systems by 1/1 CC coupling to give two isomer azanickelacyclopentanones. The nickela five-membered rings thus obtained were characterized and their reaction modes are described. Depending on the ligand present and under special reaction conditions, with continuous, slow addition of the isocyanate to a solution of propene and the (lig)Ni0 starting complex, that there is catalytic formation of crotonic acid anilide.
Journal of Catalysis, 1997
Der erste Gesch~iftsffihrer, Herr Prof. v. Krehl (Strassburg), erSffnet die Yersammlung und begri... more Der erste Gesch~iftsffihrer, Herr Prof. v. Krehl (Strassburg), erSffnet die Yersammlung und begriisst die anwesenden G~ste und Mitglieder. Sodann gedenkt er der im letzten Jahre verstorbenen friiheren Mitglieder der Yersammlung Fiirstner, Ziegler nnd Gilbert, die Anwesenden erheben sieh zum Zeiehen ehrenden Andenkens yon ihren Sitzen.
Angewandte Chemie, 2006
Analoga 1 und 6a, b sind luftempfindlich, die Dibenzo-Derivate 2a, 7,9a, b und 10 nicht. Die Oxid... more Analoga 1 und 6a, b sind luftempfindlich, die Dibenzo-Derivate 2a, 7,9a, b und 10 nicht. Die Oxidationspotentiale der Donoren (Tabelle 1) wurden durch Cyclovoltammetrie ermittelt. Die Werte fur die Donoren mit chinoiden Strukturen sind niedriger als die bei gleichen Bedingungen gemessenen Werte von TTF (0.28, 0.64 V vs. SCE), insbesondere die Stammverbindung 1 ist ein extrem guter Elektronendonator. Ursache diirfte sein, daR die chinoiden Strukturen bei einer Oxidation ein neues aromatisches Sextett bilden. Charakteristisch ist ferner die sehr kleine Differenz zwischen dem ersten und zweiten Oxidationspotential von 1 sowie, da13 in den neuen Donoren Zwei-Elektronen-Oxidationswellen beobachtet werden. Demnach Tahelle 2. Eigenschaiten von Charge-Transfer-Komplexen rnit TCNQ
Angewandte Chemie International Edition in English, 1989
Journal of Organometallic Chemistry, 1989
Fluorine-substituted alkenes such as 3,3,3-trifluoropropene (Ia) and 1,1-d& fluoroethene (Ib) und... more Fluorine-substituted alkenes such as 3,3,3-trifluoropropene (Ia) and 1,1-d& fluoroethene (Ib) undergo highly regioselective l/l CC-coupling reactions with phenylisocyanate (II) on (Lig)Ni' systems to form tricyclohexylphosphane-(2-trifluoromethyl)-5-azanickelacyclopentan-4-one (Va) and tricyclohexylphosphane-5azadifluoronickelacyclopentan-4-one (Vb). The structures of these compounds were confirmed by 'H, 13C, 31P and 19F NMR spectroscopy, which show' that the coordination geometry about nickel is approximately square planar. The reactivity of Va/Vb differs strongly from that of known alkyl-or aryl-substituted nickela-systerns, as shown by the effect of various protonolysis reagents, the reaction with electrophiles such as CO and MeI, the behaviour of Va and Vb during thermolysis. Zusammenfassuug Fluorsubstituierte Alkene, wie 3,3,3_Trifluorpropen (Ia) und l,l-Difluorethen (Ib), reagieren mit Phenylisocyanat (II) am (Lig)Ni'-System unter hoher Regioselektivitslt im Sinne einer l/l CC-Kupplung zu Tricyclohexylphosphan-(2-trifluormethyl)-5-azanickelacyclopentan-4-on (Va) und Tricyclohexylphosphan-5-aza-2difluomickelacyclopentan-4-on (Vb). Zur Strukturabsicherung dieser Verbindungen wurden IH-, 13C-, 31P-und "F-NMR-Messungen herangezogen, woraus sich eine annHhemd quadratisch-planare Koordination am Nickel ergibt. Das Reaktiosverhalten von Va/Vb unterscheidet sich stark von dem bekannter alkyl-oder arylsubstituierter Nickelacyclen. Dieses wird durch Einwirkung verschiedener Protonolysereagenzien, Umsetzung mit Elektrophilen, wie CO und MeI, und ihr Thermolyseverhalten belegt.
is described a process for the preparation of (oxy) organotin fluorides by reacting oxides or hyd... more is described a process for the preparation of (oxy) organotin fluorides by reacting oxides or hydroxides of mono- or di-organotin with hydrofluoric acid, this reaction being carried out in the presence of surfactant compounds. Application to heat insulating glazing panes and the flat heating, in particular automobile panes, of refrigeration display cases.
Die vorliegende Erfindung betrifft eine Schmierstoffzusammensetzung, die einen festen Schmierstof... more Die vorliegende Erfindung betrifft eine Schmierstoffzusammensetzung, die einen festen Schmierstoff mit Schichtgitterstruktur enthalt, der 70 bis 100 Gew.-% Zinndisulfid umfasst. Die Schmierstoffzusammensetzung besitzt ausgezeichnete Schmier- und Verschleisseigenschaften.
MRS Communications
The use of copper hydroxyphosphate (Cu 2 PO 4 OH), also called libethenite, as a near-infrared (N... more The use of copper hydroxyphosphate (Cu 2 PO 4 OH), also called libethenite, as a near-infrared (NIR) absorbing additive has been investigated. Samples were synthesized by using a hydrothermal treatment or simple wet chemical processing, which was later easily upscaled. All synthesized samples showed a strong absorption in the NIR region. Trials were conducted to produce laser-marked plastic plates and security IR ink printing tests. It was found that when incorporated in plastic and ink formulation, Cu 2 PO 4 OH added good NIR absorption properties without influencing other finished product properties too much, which confirms that it is a suitable additive that can be readily manufactured at room temperature and without pressured equipment.
ChemInform, Mar 6, 1990
ChemInform Abstract The fluorine-substituted alkenes (I) undergo highly regioselective 1:1 CC-cou... more ChemInform Abstract The fluorine-substituted alkenes (I) undergo highly regioselective 1:1 CC-coupling with phenylisocyanate (II) on Ni0 systems to form the azanickelacyclopentanones (V). As shown by NMR, the coordination geometry about nickel is approximately square planar. The reactivity of these complexes differs strongly from that of known alkyl-or arylsubstituted nickela-systems, as shown by the behavior of (V) during hydrolysis, thermolysis or reaction with electrophiles.
ChemInform, 1989
ChemInform Abstract The catalytic addition of isocyanates to CC double or triple bond compounds i... more ChemInform Abstract The catalytic addition of isocyanates to CC double or triple bond compounds is running via aza-nickela-heterocyclic intermediates of type (V) and (VI). When vinylcyclohexane (I) reacts with phenyl isocyanate (II) in the presence of Ni(cod)2 and the ligand tricyclohexylphosphane, anilides (III) and (IV) are obtained (no yields given). However, intermediates of type (V) are sometimes able to abstract intramolecularly a β-H, thus producing unsaturated products and reforming the catalyst. To test, if β-H abstraction is possible not only from the heterocyclic ring but from an exocyclic position as well, the reaction is also conducted according to A), B) or C) and indeed, depending on the ligand, the reaction is directed towards an equal abstraction from both β-positions or to a nearly unique preference of one of the two β-positions.
Synthesis and Application of Metal Methansulphonic Acid salts
Journal of Organometallic Chemistry, 1989
ABSTRACT The use of chelating ligands such as DCPE, BIPY and TMEDA as stabilizing ligands permits... more ABSTRACT The use of chelating ligands such as DCPE, BIPY and TMEDA as stabilizing ligands permits the preparation of the novel ligand-Ni complexes of 1,1-difluoroethene. The structures of the 16e complexes were confirmed by 1H, 13C, 19F and 31P NMR spectroscopy. Characteristic properties are described.
Journal of Organometallic Chemistry, 1990
ABSTRACT 1,7-Octadiene and phenylisocyanate react with the (Lig)Ni0-system, depending on the liga... more ABSTRACT 1,7-Octadiene and phenylisocyanate react with the (Lig)Ni0-system, depending on the ligand, to give differing products. Thus with tricyclohexylphosphane the reaction is accompanied by cyclization and (2-methylenecyclohexyl)acetanilide(V) is formed. On the other hand, reaction with the weakly basic tricyclohexylphosphite gives the acyclic nona-2,8-dienecarboxanilide (VI).
Journal of Organometallic Chemistry, 1988
ABSTRACT Isocyanates react with propene at ligand-nickel(0) systems by 1/1 CC coupling to give tw... more ABSTRACT Isocyanates react with propene at ligand-nickel(0) systems by 1/1 CC coupling to give two isomer azanickelacyclopentanones. The nickela five-membered rings thus obtained were characterized and their reaction modes are described. Depending on the ligand present and under special reaction conditions, with continuous, slow addition of the isocyanate to a solution of propene and the (lig)Ni0 starting complex, that there is catalytic formation of crotonic acid anilide.
Journal of Catalysis, 1997
Der erste Gesch~iftsffihrer, Herr Prof. v. Krehl (Strassburg), erSffnet die Yersammlung und begri... more Der erste Gesch~iftsffihrer, Herr Prof. v. Krehl (Strassburg), erSffnet die Yersammlung und begriisst die anwesenden G~ste und Mitglieder. Sodann gedenkt er der im letzten Jahre verstorbenen friiheren Mitglieder der Yersammlung Fiirstner, Ziegler nnd Gilbert, die Anwesenden erheben sieh zum Zeiehen ehrenden Andenkens yon ihren Sitzen.
Angewandte Chemie, 2006
Analoga 1 und 6a, b sind luftempfindlich, die Dibenzo-Derivate 2a, 7,9a, b und 10 nicht. Die Oxid... more Analoga 1 und 6a, b sind luftempfindlich, die Dibenzo-Derivate 2a, 7,9a, b und 10 nicht. Die Oxidationspotentiale der Donoren (Tabelle 1) wurden durch Cyclovoltammetrie ermittelt. Die Werte fur die Donoren mit chinoiden Strukturen sind niedriger als die bei gleichen Bedingungen gemessenen Werte von TTF (0.28, 0.64 V vs. SCE), insbesondere die Stammverbindung 1 ist ein extrem guter Elektronendonator. Ursache diirfte sein, daR die chinoiden Strukturen bei einer Oxidation ein neues aromatisches Sextett bilden. Charakteristisch ist ferner die sehr kleine Differenz zwischen dem ersten und zweiten Oxidationspotential von 1 sowie, da13 in den neuen Donoren Zwei-Elektronen-Oxidationswellen beobachtet werden. Demnach Tahelle 2. Eigenschaiten von Charge-Transfer-Komplexen rnit TCNQ
Angewandte Chemie International Edition in English, 1989
Journal of Organometallic Chemistry, 1989
Fluorine-substituted alkenes such as 3,3,3-trifluoropropene (Ia) and 1,1-d& fluoroethene (Ib) und... more Fluorine-substituted alkenes such as 3,3,3-trifluoropropene (Ia) and 1,1-d& fluoroethene (Ib) undergo highly regioselective l/l CC-coupling reactions with phenylisocyanate (II) on (Lig)Ni' systems to form tricyclohexylphosphane-(2-trifluoromethyl)-5-azanickelacyclopentan-4-one (Va) and tricyclohexylphosphane-5azadifluoronickelacyclopentan-4-one (Vb). The structures of these compounds were confirmed by 'H, 13C, 31P and 19F NMR spectroscopy, which show' that the coordination geometry about nickel is approximately square planar. The reactivity of Va/Vb differs strongly from that of known alkyl-or aryl-substituted nickela-systerns, as shown by the effect of various protonolysis reagents, the reaction with electrophiles such as CO and MeI, the behaviour of Va and Vb during thermolysis. Zusammenfassuug Fluorsubstituierte Alkene, wie 3,3,3_Trifluorpropen (Ia) und l,l-Difluorethen (Ib), reagieren mit Phenylisocyanat (II) am (Lig)Ni'-System unter hoher Regioselektivitslt im Sinne einer l/l CC-Kupplung zu Tricyclohexylphosphan-(2-trifluormethyl)-5-azanickelacyclopentan-4-on (Va) und Tricyclohexylphosphan-5-aza-2difluomickelacyclopentan-4-on (Vb). Zur Strukturabsicherung dieser Verbindungen wurden IH-, 13C-, 31P-und "F-NMR-Messungen herangezogen, woraus sich eine annHhemd quadratisch-planare Koordination am Nickel ergibt. Das Reaktiosverhalten von Va/Vb unterscheidet sich stark von dem bekannter alkyl-oder arylsubstituierter Nickelacyclen. Dieses wird durch Einwirkung verschiedener Protonolysereagenzien, Umsetzung mit Elektrophilen, wie CO und MeI, und ihr Thermolyseverhalten belegt.
is described a process for the preparation of (oxy) organotin fluorides by reacting oxides or hyd... more is described a process for the preparation of (oxy) organotin fluorides by reacting oxides or hydroxides of mono- or di-organotin with hydrofluoric acid, this reaction being carried out in the presence of surfactant compounds. Application to heat insulating glazing panes and the flat heating, in particular automobile panes, of refrigeration display cases.
Die vorliegende Erfindung betrifft eine Schmierstoffzusammensetzung, die einen festen Schmierstof... more Die vorliegende Erfindung betrifft eine Schmierstoffzusammensetzung, die einen festen Schmierstoff mit Schichtgitterstruktur enthalt, der 70 bis 100 Gew.-% Zinndisulfid umfasst. Die Schmierstoffzusammensetzung besitzt ausgezeichnete Schmier- und Verschleisseigenschaften.
MRS Communications
The use of copper hydroxyphosphate (Cu 2 PO 4 OH), also called libethenite, as a near-infrared (N... more The use of copper hydroxyphosphate (Cu 2 PO 4 OH), also called libethenite, as a near-infrared (NIR) absorbing additive has been investigated. Samples were synthesized by using a hydrothermal treatment or simple wet chemical processing, which was later easily upscaled. All synthesized samples showed a strong absorption in the NIR region. Trials were conducted to produce laser-marked plastic plates and security IR ink printing tests. It was found that when incorporated in plastic and ink formulation, Cu 2 PO 4 OH added good NIR absorption properties without influencing other finished product properties too much, which confirms that it is a suitable additive that can be readily manufactured at room temperature and without pressured equipment.