Benzene Ring Containing Patents (Class 568/17)
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Patent number: 6187953Abstract: Guanidinium phosphanes of Formula I wherein the substituents are defined as in the specification which are useful catalyst ligands for the carbon-carbon linkage reactions of the hect reaction.Type: GrantFiled: November 17, 1999Date of Patent: February 13, 2001Assignee: Celanese GmbHInventors: Othmar Stelzer, Franz Peter Schmidtchen, Antonella Hessler, Michael Tepper, Harald Dibowski, Michael Riedel, Helmut Bahrmann
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Patent number: 6169179Abstract: A method for manufacturing (3S,4R)-4-[(R)-1′-formylethyl]azetidin-2-one derivatives represented by formula (3) wherein R1 represents a hydrogen atom or a protective group, through asymmetric hydroformylation of 4-vinylazetidin-2-one represented by formula (1) wherein R1 has the same meaning as described above; in the presence of a rhodium complex and a (2S,4S)-diphosphine compound represented by formula (2) wherein R2 represents a phenyl group which may be substituted with 1-5 substituent(s) selected from a lower alkyl group, a lower alkoxy group, and a halogen atom. By use of both an inexpensive optically active diphosphine compound and a rhodium complex as catalysts, intermediate compounds important for carbapenem antibiotics can be manufactured with high selectivity and efficiency.Type: GrantFiled: June 10, 1999Date of Patent: January 2, 2001Assignee: Takasago International CorporationInventors: Howard Alper, Takao Saito, Takashi Miura
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Patent number: 6162951Abstract: Compounds of Formula (I) wherein R, R.sup.1, R.sup.2 and R.sup.9 are as herein defined, processes for their preparation and transition metal complexes comprising such compounds are disclosed. The complexes may be attached to insoluble supports and are useful as asymetric catalysts.Type: GrantFiled: March 19, 1999Date of Patent: December 19, 2000Assignee: Oxford Asymmetry International plcInventors: Mario Eugenio Cosamino Polywka, Edwin Moses, Daniel John Bayston, Anthony David Baxter, Mark Richard Ashton
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Patent number: 6160180Abstract: A compound is disclosed having the formula (I), in which m equals 1 to 1000; x equals 0 to 4; W is a group of formulas --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)CH.sub.2 -- or --CH.sub.2 CH(CH.sub.3)--; R is hydrogen, a straight-chain or branched-chain C.sub.1 -C.sub.5 alkyl radical; or a group of formulas (a) or (b), in which a, b, c, d and e independently represent a number from 0 to 1000, at least one of the numbers represented by a, b, c, d and e being higher than 0; R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are the same or different and represent hydrogen, C.sub.1 -C.sub.5 alkyl or a group of formula (c); R.sup.1 and R.sup.2 are the same or different and represent a straight-chain, a branched-chain or a cyclic C.sub.1 -C.sub.30 alkyl radical or C.sub.6 -C.sub.10 aryl radical which is non-substituted or substituted by one to five C.sub.1 -C.sub.3 alkyl radicals, or R.sup.1 and R.sup.Type: GrantFiled: April 22, 1999Date of Patent: December 12, 2000Assignee: Celanese Chemicals Europe GmbHInventors: Steffen Haber, Hans-Jerg Kleiner, Sandra Bogdanovic, Helmut Bahrmann, Carl-Dieter Frohning
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Patent number: 6124476Abstract: The present invention discloses new organic compounds (e.g., ligands), their metal complexes and compositions using those compounds. The invention also relates to the field of catalysis. In particular, this invention relates to new compounds which when combined with suitable metals or metal precursor compounds provide useful catalysts for various bond-forming reactions, including Suzuki cross-coupling reactions. The invention also relates to performing Suzuki cross coupling reactions with unreactive aryl-chlorides.Type: GrantFiled: February 18, 1999Date of Patent: September 26, 2000Assignee: Symyx Technologies, Inc.Inventors: Anil Guram, Xiaohong Bei, Timothy S. Powers, Bernd Jandeleit, Thomas Crevier
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Patent number: 6121495Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.Type: GrantFiled: September 12, 1996Date of Patent: September 19, 2000Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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Patent number: 6121494Abstract: Reacting a lead tetraacetate with an optically active phosphine oxide carboxylic acid represented by the following general formula (1): ##STR1## in order to obtain an optically active vinyl phosphine oxide represented by the following general formula (2): ##STR2##Type: GrantFiled: December 9, 1999Date of Patent: September 19, 2000Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Masashi Sugiya, Hiroyuki Nohira
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Patent number: 6103867Abstract: The catalyst systems comprise as active constituentsa) a metal complex of the formula (I) ##STR1## b) one or more Lewis or protic acids or a mixture of Lewis and protic acids.Type: GrantFiled: June 8, 1999Date of Patent: August 15, 2000Assignee: BASF AktiengesellschaftInventors: Michael Slany, Arthur Hohn
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Patent number: 6084133Abstract: A process for producing a secondary phosphine of formula (2) ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each represent an alkyl group, a cycloalkyl group or an aryl group, each of the above groups being optionally substituted by an alkyl group, an alkoxy group, a halogen atom, a perfluoroalkyl group, an amino group or a phosphino group, which comprises reacting a phosphine halide of formula (1) ##STR2## wherein R.sup.1 and R.sup.2 are as defined above and X represents a halogen atom, with a metal selected from the metals of Groups 2 to 15 in the Periodic Table or an alloy thereof and reacting the resultant metal di-substituted phosphide with an agent for protonation.Type: GrantFiled: September 30, 1999Date of Patent: July 4, 2000Assignee: Kankyo Kagaku Center Co., Ltd.Inventor: Masatoshi Kawashima
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Patent number: 6075154Abstract: A novel phosphine compound usable as a catalyst in various asymmetric synthetic reactions is disclosed. The compound is a 2,2'-bis(diarylphosphino)-6,6'-bis(trifluoromethyl)-1,1'-biphenyl of (1): ##STR1## where R is a phenyl group or a phenyl group substituted by lower alkyl group, lower alkoxy group, halogen atom, or lower haloalkyl group.Type: GrantFiled: July 30, 1998Date of Patent: June 13, 2000Assignee: Takasago International CorporationInventors: Yoshiharu Gonda, Yoji Hori, Akio Yamaguchi, Toshimitsu Hagiwara
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Patent number: 6043396Abstract: Phospholanes and diphospholanes of the formula I ##STR1## where: R.sup.1 and R.sup.2 are, independently of one another, C.sub.1 -C.sub.6 -alkyl, aryl, alkylaryl,R.sup.1 is also hydrogen,A is either R.sup.1 or ##STR2## B is a linker having 1-5 carbon atoms between the two phosphorus atoms, and their use as catalyst in asymmetric synthesis.Type: GrantFiled: June 8, 1998Date of Patent: March 28, 2000Assignee: BASF AktiengesellschaftInventors: Rainer Sturmer, Armin Borner, Jens Holz, Gudrun Voss
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Patent number: 6040461Abstract: The invention relates to a process for the preparation of vitamin D.sub.3 compounds of formula I. ##STR1## Wherein A is a single or a double bond; B is a single, cis-double, trans double or a triple bond; R.sub.1 and R.sub.2 are independently hydrogen, a lower alkyl, e.g., a C.sub.1 -C.sub.4 alkyl; R.sub.3 and R.sub.4 are independently a lower alkyl, e.g., C.sub.1 -C.sub.4 alkyl, a hydroxyalkyl, and a haloalkyl, e.g., a fluoroalkyl; and X and Y are independently hydrogen or hydroxy in the case when B is a single or a double bond.Type: GrantFiled: May 11, 1999Date of Patent: March 21, 2000Assignees: Hoffmann-La Roche Inc., Syntex (U.S.A.)Inventors: Andrew David Batcho, Percy Sarwood Manchand, Milan Radoje Uskokovic
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Patent number: 6037500Abstract: The present invention relates to rigid chiral ligands usefull in making catalysts for asymmetric synthesis. More particularly, the present invention relates to new monodentate and bidentate cyclic chiral phosphine ligands which are formed into catalysts to provide high selectivity of the enantiomeric structure of the end-product.Type: GrantFiled: June 13, 1997Date of Patent: March 14, 2000Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 6020343Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.Type: GrantFiled: June 15, 1998Date of Patent: February 1, 2000Assignee: Merck Frosst Canada, Inc.Inventors: Michel Belley, Jacques Yves Gauthier, Erich Grimm, Yves LeBlanc, Chun-Sing Li, Michel Therien, Cameron Black, Petpiboon Prasit, Cheuk-Kun Lau, Patrick Roy
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Patent number: 6020528Abstract: Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.20 alkyl, cyclopentyl, cyclohexyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.18 alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C.sub.1 -C.sub.4 alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy with the provisos that at least one of the radicals R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is other than hydrogen and that, if R.sub.1 and R.sub.2 are methyl, R.sub.3 and R.sub.6 are not methyl, and mixtures of such compounds with .alpha.-hydroxy ketones, benzophenones and .alpha.-amino ketones, are suitable as photoinitiators.Type: GrantFiled: February 26, 1997Date of Patent: February 1, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Manfred Kohler, Andreas Valet
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Patent number: 5994587Abstract: A process for the purification of crude neomenthyldiphenylphosphine, the process comprising crystallizing the crude neomenthyldiphenylphosphine using a solvent consisting essentially of methanol. The process provides for the unexpectedly efficient production of neomenthyldiphenylphosphine having purities of at least 97 mole percent, and more preferably at least about 99 mole percent. Another embodiment of the invention is neomenthyldiphenylphosphine having a purity of at least 97 mole percent produced by crystallizing crude neomenthyldiphenylphosphine having a purity of less than 97 mole percent using a solvent consisting essentially of methanol.Type: GrantFiled: May 26, 1998Date of Patent: November 30, 1999Assignee: Albemarle CorporationInventors: Tse-Chong Wu, K. Pushpananda A. Senaratne
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Patent number: 5972825Abstract: The present invention relates to compounds of the formula (I) ##STR1## where R.sup.1 is H or an alkyl radical having from 1 to 12 carbon atoms, R.sup.2 is a straight-chain alkylene radical having from 1 to 8 carbon atoms, an oxygen-containing alkylene radical having from 2 to 4 carbon atoms, a radical of the formula (II) or (III) ##STR2## or a cycloalkylene radical having from 3 to 10 carbon atoms, R.sup.3 is an alkyl radical having from 1 to 25 carbon atoms or an aryl radical having from 6 to 10 carbon atoms, A is a radical --COO.sup.- or --SO.sub.3 .sup.- and x=0, y=1, m=1 and n=1, or x=1, y=1, m=(1 or 2) and n=(1 or 2), or, if R.sup.2 is a radical of the formula (II) or (III), x=1, y=0, m=(0 or 1) and n=(0 or 1), and also a process for their preparation.Type: GrantFiled: June 10, 1998Date of Patent: October 26, 1999Assignee: Celanese GmbHInventors: Dieter Regnat, Hans-Jerg Kleiner, Helmut Bahrmann
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Covalent lipid-phosphono-carboxylic acid conjugates and application thereof as antiviral medicaments
Patent number: 5955452Abstract: The present invention concerns new lipid derivatives of phosphonocarboxylic acids of the general formula I, ##STR1## in which the meaning of the symbols is elucidated in the description, tautomers thereof and their physiologically tolerated salts of inorganic and organic bases as well as processes for the production thereof and pharmaceutical agents containing these compounds.Type: GrantFiled: August 26, 1998Date of Patent: September 21, 1999Assignee: Roche Diagnostics GmbHInventors: Harald Zilch, Dieter Herrmann, Hans-George Opitz, Gerd Zimmermann, Edgar Voss -
Patent number: 5952525Abstract: The trimethylsulphonium salt of N-phosphonomethylglycine is prepared by reacting N-phosphonomethylglycine, preferably in the form of a solid, with an aqueous solution of trimethylsulphonium carbonate or trimethylsulphonium bicarbonate or a mixture thereof. The trimethylsulphonium carbonate or trimethylsulphonium bicarbonate may be prepared by bubbling carbon dioxide through an aqueous solution of trimethylsulphonium hydroxide. It is possible to manufacture trimethylsulphonium carbonate or bicarbonate at one site and then transport them to a different site for local manufacture of N-phosphonomethylglycine in a relatively unsophisticated plant which produces minimal effluent.Type: GrantFiled: May 8, 1998Date of Patent: September 14, 1999Assignee: ZENECA LimitedInventors: Brian Geoffrey Cox, Stephen Martin Brown, Thomas Gray
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Patent number: 5942637Abstract: Compounds containing a tetradecachlorocyclohexasilane dianion are prepared by contacting trichlorosilane with a reagent composition comprising a tertiary polyamine. The compound ?pedeta.SiH.sub.2 Cl.sup.+1 !.sub.2 ?Si.sub.6 Cl.sub.14.sup.-2 ! wherein pedeta is N,N,N',N",N"-pentaethyldiethylenetriamine is prepared by contacting trichlorosilane with pedeta. The compound ?Ph.sub.4 P.sup.+1 !.sub.2 ?Si.sub.6 Cl.sub.14.sup.-2 ! is prepared by contacting trichlorosilane with a mixture of N,N,N',N'-tetraethylethylenediamine and triphenylphosphonium chloride. The tetradecachlorocyclohexasilane dianion can be chemically reduced to cyclohexasilane, a compound useful in the deposition of amorphous silicon films. The tetradecachlorcyclohexasilane dianion can also be contacted with a Grignard reagent to form a dodecaorganocyclohexasilane.Type: GrantFiled: March 30, 1998Date of Patent: August 24, 1999Assignee: North Dakota State University Research FoundationInventors: Philip Raymond Boudjouk, Beon-Kyu Kim, Michael Perry Remington, Bhanu Chauhan
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Patent number: 5932770Abstract: A process for separating off phosphine oxides and alkylarylphosphines from an organic reaction mixture of a homogeneous hydroformylation carried out with the use of a catalyst system, which reaction mixture contains organometallic complex compounds and, in a molar excess, ammonium salts of aromatic phosphines as ligands comprising subjecting the organic reaction mixture to an extraction treatment with a 0.001-0.5% strength by weight of an alkali metal hydroxide or alkaline earth metal hydroxide solution and separating off the aqueous phase containing the phosphine oxides and alkylarylphosphines to decrease markedly the concentration of the phosphine oxides and alkylarylphosphines in the hydroformylation mixture, which process is particularly suitable for continuously operated hydroformylations.Type: GrantFiled: August 11, 1997Date of Patent: August 3, 1999Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Thomas Muller
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Patent number: 5922918Abstract: The present invention provides a method for making compound (1) by reacting compound (2) with phosphine oxide (3) in the presence of a transition metal/phosphine complex and optionally reducing the reaction product: ##STR1## where n represents 0 or 1; the double line having a continuous line and a dotted line represents a double bond or a single bond such that the ring having the double line forms a naphthalene ring or an octahydronaphthalene ring with an adjacent benzene ring; Tf represents a trifluoromethanesulfonyl group; and Ar represents a phenyl group, a substituted phenyl group or a naphthyl group. The present invention provides an economical way to produce compound (1) as a ligand of a complex useful as a catalyst for a variety of asymmetric synthesis reactions.Type: GrantFiled: October 24, 1997Date of Patent: July 13, 1999Assignee: Takasago International CorporationInventors: Xiaoyaong Zhang, Noboru Sayo
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Patent number: 5919984Abstract: This invention concerns a process for the selective mono oxidation of organic tertiary polyphosphines to phosphine monooxides. These monooxides are useful as ligands for transition metals in the formation of transition metal catalysts.Type: GrantFiled: April 17, 1998Date of Patent: July 6, 1999Inventor: Vladimir Grushin
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Patent number: 5908931Abstract: The present invention relates particularly to novel preorganized hexadentate ligands that are suitable for completing with a radionuclide, and are useful as general imaging agents for diagnostic purposes.Type: GrantFiled: December 14, 1990Date of Patent: June 1, 1999Assignee: Mallinckrodt Inc.Inventors: Raghavan Rajagopalan, William L. Neumann, Dennis L. Nosco
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Patent number: 5902904Abstract: The invention is an improved method for the preparation of tertiary phosphines by way of cross-coupling of aryl, alkenyl, cycloalkenyl or aralkyl halides or aryl, alkenyl, cycloalkenyl or aralkyl sulfonate esters with chlorophosphines in the presence of a catalyst and a reductant. The general reaction scheme is shown below: ##STR1## wherein R.sup.1 is aryl, alkenyl, cycloalkenyl or aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl, or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; R.sup.2 and R.sup.3 are independently aryl, alkyl, aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; and n is 2 where R.Type: GrantFiled: August 21, 1998Date of Patent: May 11, 1999Assignee: Monsanto CompanyInventors: Scott A. Laneman, David J. Ager, Amihia Eisenstadt
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Patent number: 5874629Abstract: New chiral biphosphines, e.g., ##STR1## are useful as key components in catalysts for asymmetric reactions, providing desirably high enantiomeric excess (ee).Type: GrantFiled: June 9, 1997Date of Patent: February 23, 1999Assignee: Merck & Co., Inc.Inventors: Philip Pye, Kai Rossen, Ralph P. Volante
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Patent number: 5874628Abstract: The invention is an improved method for the preparation of tertiary phosphines by way of cross-coupling of aryl, alkenyl, cycloalkenyl or aralkyl halides or aryl, alkenyl, cycloalkenyl or aralkyl sulfonate esters with chlorophosphines in the presence of a catalyst and a reductant. The general reaction scheme is shown below: ##STR1## wherein R.sup.1 is aryl, alkenyl, cycloalkenyl or aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl, or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; R.sup.2 and R.sup.3 are independently aryl, alkyl, aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl or CoNR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; and n is 2 where R.Type: GrantFiled: March 26, 1997Date of Patent: February 23, 1999Assignee: Monsanto CompanyInventors: Scott A. Laneman, David J. Ager, Amihia Eisenstadt
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Patent number: 5872273Abstract: A novel diphosphine compound of the formula (I): ##STR1## where R.sup.1 and R.sup.2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.Type: GrantFiled: December 22, 1997Date of Patent: February 16, 1999Assignee: Takasago International CorporationInventors: Takao Saito, Tohru Yokozawa, Xiaoyaong Zhang, Noburo Sayo
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Patent number: 5866720Abstract: (1) Alkali metal diarylphosphides are formed by mixing triarylphosphine with, and preferably introducing triarylphosphine into, a two-phase mixture one or more alkali metals, preferably a mixture or alloy of sodium and potassium, in an anhydrous organic liquid diluent in the presence of molecular hydrogen. (2) To form a cycloalkyldiarylphosphine, at least a portion of the reaction mixture formed as in (1) (or alkali metal diarylphosphide recovered therefrom) and cycloalkyl mesylate or tosylate are mixed together and maintained under suitable reaction conditions. Reaction (2) is driven by the presence of residual sodium from reaction (1). Conduct of reaction (2) under a hydrogen atmosphere suppresses undesirable side reactions.Type: GrantFiled: April 29, 1998Date of Patent: February 2, 1999Assignee: Albemarle CorporationInventors: William J. Layman, Jr., George W. Welsh
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Patent number: 5855867Abstract: A compound and method of making a compound for use as a diagnostic or therapeutic pharmaceutical comprises at least one functionalized hydroxyalkyl phosphine donor group and one or more sulfur or nitrogen donor and a metal combined with the ligand.Type: GrantFiled: March 14, 1997Date of Patent: January 5, 1999Assignee: The Curators of the University of MissouriInventors: Kattesh V. Katti, Srinivasa Rao Karra, Douglas E. Berning, C. Jeffrey Smith, Wynn A. Volkert, Alan R. Ketring
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Patent number: 5856558Abstract: The present invention relates to novel stabilized phosphorous ylides and processes for their preparation. More particularly, the present invention relates to a process for substituting the carbonyl oxygen of 2-formyl- or 2-oxoalkylidenetriphenyl-phosphoranes (OATP) by other stabilizing groups to form novel compounds having an increased tendency to form complexes or compounds which absorb in the visible region of the spectrum.The compounds according to the present invention areCompounds of the formula (1)Ph.sub.3 .dbd.CH--C(R).dbd.Nu (1)wherein R is hydrogen, a C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.3 -fluoroalkyl or perfluoroalkyl radical, an unfluorinated or fluorinated C.sub.6 -C.sub.14 -aryl radical or a group OCH.sub.3 ; andNu is S, Se, C(CN).sub.2, NH, PhN, PhNHN, ##STR1## or a radical of the formulae (a), (b), (c), (d) or (e) ##STR2## wherein Z is C(CH.sub.3).sub.2, S or N(CH.sub.3) and n=1 or 2 (provided that the combinations R.dbd.Ar, SAlk or OAlk and Nu.dbd.NPh, and the combinations R.dbd.Type: GrantFiled: August 18, 1997Date of Patent: January 5, 1999Assignee: Hoechst AktiengesellschaftInventors: Sergej Pasenok, Wolfgang Appel
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Patent number: 5852212Abstract: Optically active .alpha.-bromo- or .alpha.-chlorocarboxylic compounds of the formula ##STR1## wherein X is bromine or chlorine;M is hydrogen, NR.sub.4.sup.+1 or a cation of an alkali or alkaline earth metal;R.sup.1 is hydrogen or lower alkyl;n is 0 or 1;R is hydrogen, C.sub.1 -C.sub.20 alkyl, or C.sub.1 -C.sub.20 alkyl substituted in the terminal position with --NR.sup.2.sub.2, --COOR.sup.2, --OR.sup.3, a free or protected --CHO group or a ring A;R.sup.2 is hydrogen or a lower alkyl;R.sup.3 is hydrogen or a protecting group;ring A is an unsubstituted or substituted ring; and* is a center of chirality,are prepared by enantioselectively hydrogenating, in the presence of a ruthenium complex of an optically active diphosphine ligand, a (Z)-.alpha.,.beta.-unsaturated compound of the general formula ##STR2## wherein R, n, X and M are as defined above.Type: GrantFiled: June 12, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventors: Emil Albin Broger, Richard Buchecker, Yvo Crameri, Teodor Lukac
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Patent number: 5847222Abstract: The present invention provides a ligand for a novel catalyst superior in such characteristics as selectivity (chemoselectivity and enantioselectivity) and catalytic activity in asymmetric synthesis reactions and a ligand for a novel catalyst effective in an asymmetric hydrogenation reaction in particular. The ligand is an optically active diphosphine compound represented by the following formula: ##STR1## where Ph is a phenyl group, X is a chlorine or bromine atom, and R.sup.1 and R.sup.2 are each an alkyl group having 1 to 3 carbon atoms.Type: GrantFiled: August 26, 1997Date of Patent: December 8, 1998Assignee: Takasago International CorporationInventors: Tohru Yokozawa, Noboru Sayo, Kazuhiko Matsumura, Hidenori Kumobayashi
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Patent number: 5847200Abstract: New diphosphines in the form of ammonium carboxylates, sulfonates or phosphonates having a singly or multiply charged diphosphine anion and the corresponding number of ammonium cations as counter ions, and a process for their preparation useful as ligand in rhodium catalyst systems for hydroformylation of olefins.Type: GrantFiled: April 17, 1997Date of Patent: December 8, 1998Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Thomas Muller
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Patent number: 5817848Abstract: The invention relates to a bidentate phosphine ligand, the phosphorus atoms of the phosphine being connected via a bridge group, the bridge group of the bidentate phosphine ligand consisting of an ortho-anellated annular system, comprising two aryl groups, which aryl groups are connected by two bridges, the first bridge consisting of an --O-- or an --S-- atom and the second bridge being a group that contains an oxygen, sulphur, nitrogen, silicon or carbon atom or a combination of these atoms, the two phosphorus atoms being connected to the two aryl groups of the bridge group at the ortho-position relative to the --O-- or --S-- atom of the first bridge.The invention also relates to the use of this bidentate phosphium ligand in a catalyst system comprising also a transition metal compound which is used in the following type of reactions: hydroformylation hydrogenation, hydrocyanation, polymerization, isomerisation, carboxylation, cross coupling and metathesis.Type: GrantFiled: November 6, 1996Date of Patent: October 6, 1998Assignee: DSM N.V.Inventors: Paulus C. J. Kamer, Mirko Kranenburg, Petrus W. N. M. van Leeuwen, Johannes G. de Vries
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Patent number: 5808163Abstract: The invention relates to chiral tertiary alkyldiarylphosphines of the formula (I), ##STR1## where: R.sup.1 is (C.sub.1 -C.sub.4)alkyl, which can also be substituted by F, CF.sub.3, OCH.sub.3,Ar.sup.1, Ar.sup.2 are phenyl, naphthyl, anthracenyl, which can also bear one or more substituents selected from the group consisting of (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, CF.sub.3, F,* designates the chiral carbon atom which can have either an (R) or an (S) configuration,and also a process for preparing these compounds.Type: GrantFiled: July 17, 1996Date of Patent: September 15, 1998Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hans Millauer, Peter Brungs
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Patent number: 5808162Abstract: A novel chiral unsymmetric diphosphine compound of formula (I): ##STR1## wherein Ar.sup.1 and Ar.sup.2, which are different from each other, each represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a furfuryl group, a benzofurfuryl group, a thienyl group, or a benzothienyl group, and a transition metal complex containing the diphosphine compound as a ligand. The complex catalyzes various asymmetric synthesis reactions, e.g., asymmetric hydrogenation or asymmetric hydrosilylation, exhibiting excellent performance in selectivity, conversion and catalytic activity, to provide a product of desired absolute configuration at high optical purity and in high yield.Type: GrantFiled: July 18, 1996Date of Patent: September 15, 1998Assignee: Takasago International CorporationInventors: Noboru Sayo, Xiaoyong Zhang, Tatsuya Omoto, Tohru Yokozawa, Tetsuro Yamasaki, Hidenori Kumobayashi
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Patent number: 5801263Abstract: Tertiary phosphines of the formula (I) ##STR1## in which X is a phosphinate or phosphonate group, are prepared by a palladium-catalyzed coupling of p-, m- or o-bromofluorobenzenes with alkyl akylphosphonous acid ester or alkyl alkylphosphite ester and reacting the resulting alkyl fluorophenylphosphinates or alkyl fluorophenylphosphonates with a metal phosphide.Type: GrantFiled: May 15, 1997Date of Patent: September 1, 1998Assignee: Hoechst AktiengesellschaftInventors: Thomas Seitz, Steffen Haber, Hans-Jerg Kleiner
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Patent number: 5801287Abstract: The present invention relates to compounds of the formula (I) ##STR1## where R.sup.1 is H or an alkyl radical having from 1 to 12 carbon atoms, R.sup.2 is a straight-chain alkylene radical having from 1 to 8 carbon atoms, an oxygen-containing alkylene radical having from 2 to 4 carbon atoms, a radical of the formula (II) or (III) ##STR2## or a cycloalkylene radical having from 3 to 10 carbon atoms, R.sup.3 is an alkyl radical having from 1 to 25 carbon atoms or an aryl radical having from 6 to 10 carbon atoms, A is a radical --COO.sup.- or --SO.sub.3.sup.- and x=0, y=1, m=1 and n=1, or x=1, y=1, m=(1 or 2) and n=(1 or 2), or, if R.sup.2 is a radical of the formula (II) or (III), x=1, y=0, m=(0 or 1) and n=(0 or 1), and also a process for their preparation.Type: GrantFiled: March 10, 1997Date of Patent: September 1, 1998Inventors: Dieter Regnat, Hans-Jerg Kleiner, Helmut Bahrmann
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Patent number: 5792884Abstract: Tertiary phosphines (I) are prepared by reducing the corresponding phosphine oxides (IIa) or phosphine dihalides (IIb) using silicon or a silicon alloy as reducing agent.Type: GrantFiled: December 21, 1993Date of Patent: August 11, 1998Assignee: BASF AktiengesellschaftInventor: Thomas Wettling
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Patent number: 5789609Abstract: Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.Type: GrantFiled: October 22, 1997Date of Patent: August 4, 1998Assignee: Takasago International CorporationInventors: Kyoko Tamao, Koji Inagaki, Noboru Sayo
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Patent number: 5789623Abstract: The present invention relates to a hydroxybiarylphosphines of the formula ##STR1## in which Ar-Ar is biphenyl, 1-phenyinaphthyl or 1,1'-binaphthyl, R.sup.1 and R.sup.2 are identical or different and are F or alkoxy having in each case 1 to 8 carbon atoms or are substituted or unsubstituted aryl, a and b are identical or different and are an integer from 0 to 4, in which R.sup.3 and R.sup.4 are identical or different and are alkyl having 1 to 8 carbon atoms, cycloalkyl having 4 to 10 carbon atoms, alkaryl having 7 to 9 carbon atoms, Ar.sup.3 --(R.sup.5).sub.n, in which A.sup.3 is an aryl radical having 6 to 10 carbon atoms, R.sup.5 is CF.sub.3, dialkylamino having a total of 2 to 8 carbon atoms or --CH.sub.2 N(alkyl).sub.2 having 1 to 3 carbon atoms per alkyl and n is an integer from 0 to 5, or --R.sup.3 --R.sup.Type: GrantFiled: June 11, 1996Date of Patent: August 4, 1998Assignee: Hoechst AktiengesellschaftInventors: Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5789624Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbomane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: April 10, 1996Date of Patent: August 4, 1998Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5786496Abstract: The present invention provides a new tetradentate bis-amido bis-alkoxo, 1,2-(bis-2,20diphenyl-2-hydroxyethanamido)benzene (H.sub.4 PHAB) and various derivatives thereof. This ligand is able to stabilize high valen metal oxo complexes by providing strong sigma donor ligands and through the use of steric bulk to prevent decomposition via formation of the .mu.-oxo dimers. Disclosed are novel metal oxo structural chemistry and oxidation reactions carried out with the novel metal oxo complexes.Type: GrantFiled: November 15, 1996Date of Patent: July 28, 1998Assignee: Northwestern UniversityInventors: Thomas V. O'Halloran, Frederick M. MacDonnell, Nathanael L. P. Fackler
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Patent number: 5777169Abstract: (1) Alkali metal diarylphosphides are formed by mixing triarylphosphine with, and preferably introducing triarylphosphine into, a two-phase mixture one or more alkali metals, preferably a mixture or alloy of sodium and potassium, in an anhydrous organic liquid diluent in the presence of molecular hydrogen. (2) To form a cycloalkyldiarylphosphine, at least a portion of the reaction mixture formed as in (1) (or alkali metal diarylphosphide recovered therefrom) and cycloalkyl mesylate or tosylate are mixed together and maintained under suitable reaction conditions. Reaction (2) is driven by the presence of residual sodium from reaction (1). Conduct of reaction (2) under a hydrogen atmosphere suppresses undesirable side reactions.Type: GrantFiled: July 1, 1997Date of Patent: July 7, 1998Assignee: Albemarle CorporationInventors: William J. Layman, Jr., George W. Welsh
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Patent number: 5773661Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: September 2, 1997Date of Patent: June 30, 1998Assignee: Celanese International CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5767317Abstract: The present invention relates to a process for preparing 2,2'-bis(diphenylphosphinylmethyl)-1,1'-binaphthyls by reacting a reaction mixture prepared in a solvent by reaction of 2,2'-dimethyl-1,1'-binaphthyl with a brominating agent to produce a mixture comprising 2,2'-bis(bromomethyl)-1,1'-binaphthyl and further brominated binaphthyls and optionally further comprising unreacted brominating agent, reacted brominating agent and solvent, with an alkyl diphenylphosphinite of the formula RO--P(Ph--(R').sub.n).sub.2, where R is an alkyl radical having from 1 to 5 carbon atoms, Ph is phenyl, R' is an alkyl radical having from 1 to 4 carbon atoms, CF.sub.3, fluorine, chlorine or bromine and n is 0, 1 or 2, at from 70.degree. to 180.degree. C. optionally in the presence of a further solvent.Type: GrantFiled: March 27, 1997Date of Patent: June 16, 1998Assignee: Hoechst AktiengesellschaftInventors: Hans-Jerg Kleiner, Dieter Regnat, Horst Roschert
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Patent number: 5756848Abstract: The invention relates to a process for preparing secondary arylphosphine oxides of the formula (I) ##STR1## in which R.sup.1 to R.sup.3, independently of one another are hydrogen, halogen, trifluoromethyl, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, di(C.sub.1 -C.sub.6)alkylamino, or diphenylamino and R.sup.4 is (C.sub.1 -C.sub.12)alkyl, cycloalkyl or aralkyl or the grouping ##STR2## which comprises reacting arylphosphinous alkyl esters of the formula (II) ##STR3## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given above and R.sup.5 is (C.sub.1 -C.sub.4)alkyl, with water at elevated temperature, in a molar ratio of phosphinous ester to water of 1:1 to 1:1.5.Type: GrantFiled: November 4, 1996Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 5756854Abstract: A process for the hydroformylation of olefinically unsaturated compounds whose hydroformylation products are insoluble or only sparingly soluble in water, comprising reacting the olefinically unsaturated compounds at 60.degree. to 180.degree. C. and 1 to 35 MPa with carbon monoxide and hydrogen in a homogeneous phase in a polar organic solvent and in the presence of a catalyst system comprising a rhodium carbonyl compound and a salt of a sulfonated or carboxylated organic monophosphine or polyphosphine, which salt is soluble both in the polar organic solvent and in water, distilling off the polar organic solvent from the reaction mixture and separating the catalyst system from the distillation residue by extraction with water.Type: GrantFiled: August 26, 1996Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Bernhard Fell, Zhigao Xia, Subba Kanagasabapathy
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Patent number: 5728886Abstract: Phosphines of the formula (I) and the preparation of these phosphines ##STR1## where Ar--Ar is a biphenyl radical, a 1-phenylnaphthyl radical or a 1,1'-binaphthyl radical, the CH.sub.2 group and the CH.sub.3 radical are each in the ortho position to the Ar--Ar bond, R is F, an alkyl radical or alkoxy radical each having from 1 to 8 carbon atoms, n is an integer from 0 to 4, R.sup.1 and R.sup.2 independently of one another, are an alkyl radical having from 1 to 10 carbon atoms, a cycloaliphatic radical having from 5 to 10 carbon atoms, or a radical Ar.sup.1 -(R.sup.3).sub.m, where Ar.sup.1 is a phenyl or naphthyl radical, R.sup.3 is F, Cl, CF.sub.3, SO.sub.3 H, SO.sub.3 Me (Me=Li, Na or K), a dialkylamino radical having from 2 to 8 carbon atoms, an alkyl radical or alkoxy radical each having from 1 to 8 carbon atoms and m is an integer from 0 to 5, or R.sup.1 and R.sup.2 together with the phosphorus atom form a 4-membered to 8-membered ring to which can be fused.Type: GrantFiled: August 3, 1995Date of Patent: March 17, 1998Assignee: Hoechst AGInventors: Christoph Naumann, Dieter Regnat