Patents by Inventor Reuben D. Rieke
Reuben D. Rieke has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20110136973Abstract: A polymer comprising the group of the formula (I) in particular derivatives of Poly[benzothiophen-2.6-diyl].Type: ApplicationFiled: July 31, 2009Publication date: June 9, 2011Applicants: BASF SE, RIEKE METALS ,INC.Inventors: Marcel Kastler, Florian Doetz, Junsik Lee, Reuben D. Rieke
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Publication number: 20100234478Abstract: Methods of preparing conducting polymers and the conductive polymers prepared therefrom are provided. The method includes a) combining a monomer-metal complex together with a manganese (II) halide to provide a monomer-manganese complex, and b) combining the monomer-manganese complex together with a metal catalyst to provide the conductive polymer. Electronic devices can be made using the polymers prepared as described herein.Type: ApplicationFiled: October 29, 2007Publication date: September 16, 2010Applicants: BASE SE, RIEKE METALS, INC.Inventor: Reuben D. Rieke
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Publication number: 20100206613Abstract: Methods of preparing conducting polymers and the conductive polymers prepared therefrom are provided. Electronic devices can be made using the polymers prepared as described herein. A method of preparing a conducting polymer is disclosed comprising: combining a di(C2-C12)alkyl metal reagent together with a first dihalo-monomer and an optional second dihalo-monomer to form a monomer-metal complex; and combining the monomer-metal complex together with a metal catalyst to provide the conducting polymer, wherein each dihalo-monomer is independently an aromatic or heteroaromatic group substituted by two halogens wherein the halogens are the same or different.Type: ApplicationFiled: October 24, 2008Publication date: August 19, 2010Applicants: BASF SE, RIEKE METALS, INC.Inventor: Reuben D. Rieke
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Publication number: 20040224364Abstract: The invention includes compounds of formula I:Type: ApplicationFiled: May 7, 2004Publication date: November 11, 2004Applicant: Rieke Metals, INc.Inventor: Reuben D. Rieke
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Patent number: 5964919Abstract: A novel zerovalent zinc species and an organozinc reagent are disclosed. The zerovalent zinc species is directly produced by reaction of a reducing agent on a zinc salt, preferably Zn(CN).sub.2. The organozinc regent results from the reaction of the zerovalent zinc species and an organic compound having one or more stable anionic leaving groups. These organozinc reagents include a wide spectrum of functional groups in the organic radical, and are useful in a variety of reactions schemes.Type: GrantFiled: May 2, 1995Date of Patent: October 12, 1999Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5852200Abstract: Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.Type: GrantFiled: August 22, 1996Date of Patent: December 22, 1998Assignee: Rieke Metals, Inc.Inventor: Reuben D. Rieke
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Patent number: 5756653Abstract: A novel zerovalent zinc species and an organozinc reagent are disclosed. The zerovalent zinc species is directly produced by reaction of a reducing agent on a zinc salt, preferably Zn(CN).sub.2. The organozinc reagent results from the reaction of the zerovalent zinc species and an organic compound having one or more stable anionic leaving groups. These organozinc reagents include a wide spectrum of functional groups in the organic radical, and are useful in a variety of reactions schemes.Type: GrantFiled: May 2, 1995Date of Patent: May 26, 1998Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5581004Abstract: The magnesium complexes of cyclic hydrocarbons and conjugated dienes, such as 1,2-dimethylenecycloalkanes and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.-lactones, including spiro .Type: GrantFiled: October 17, 1994Date of Patent: December 3, 1996Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5507973Abstract: Novel zerovalent metal species and organometallic reagents are disclosed. The zerovalent metal species are directly produced by reaction of a reducing agent on a metal cyanide salt. Preferably, the zerovalent metal species are directly produced by reaction of an alkali metal reducing agent with a metal cyanide salt. The organometallic reagent results from the reaction of the zerovalent metal species and an organic compound having one or more stable anionic leaving groups.Type: GrantFiled: June 4, 1992Date of Patent: April 16, 1996Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5498734Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.Type: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5490952Abstract: A novel zerovalent copper species and an organocopper reagent are disclosed. The zerovalent copper species is directly produced by reaction of a reducing agent with a combination of copper cyanide or halide and an alkali metal halide salt. The organocopper reagent resulting from the reaction of the zerovalent copper species and an organic compound having one or more stable anionic leaving groups is a stable reagent that will not significantly homocouple and under controlled conditions tolerates the presence of nitrile, epoxide, imine, enone, ketone, ester, allyl and benzyl groups within the organo radical. The reagent can be controlled so that it will selectively add to an organic electrophile such as an acid halide or aldehyde while other less reactive electrophilic groups are present. The reagent will also add under controlled conditions to epoxide, enone, imine and ketone groups.Type: GrantFiled: April 23, 1992Date of Patent: February 13, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5490951Abstract: A novel zerovalent copper species and an organocopper reagent are disclosed. The zerovalent copper species is directly produced by reaction of a reducing agent with a combination of copper(I) cyanide or halide and an alkali metal halide salt. The organocopper reagent resulting from the reaction of the zerovalent copper species and an organic compound having one or more stable anionic leaving groups is a stable reagent that will not significantly homocouple and under controlled conditions tolerates the presence of nitrile, epoxide, imine, enone, ketone, ester, allyl and benzyl groups within the organo radical. The reagent can be controlled so that it will selectively add to an organic electrophile such as an acid halide or aldehyde while other less reactive electrophilic groups are present. The reagent will also add under controlled conditions to epoxide, enone, imine and ketone groups.Type: GrantFiled: March 23, 1993Date of Patent: February 13, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5463018Abstract: Polycarbynes, such as doped polycarbynes, prepared from a soluble source of electrons and an organic monomer or co-monomer containing at least one carbyne group and, optionally, containing a doping agent, in an ethereal, polyethereal, or hydrocarbon solvent are presented. A wide variety of arylcarbyne and/or alkylcarbyne monomers and co-monomers can be combined with a source of electrons soluble in an ethereal, polyethereal, or hydrocarbon solvent to form novel polycarbyne polymers. These polycarbyne polymers can be used to form synthetic diamond materials, fibers, and other materials that can withstand extreme conditions.Type: GrantFiled: January 25, 1994Date of Patent: October 31, 1995Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5436315Abstract: Polycarbynes prepared from a soluble source of electrons and an organic monomer or co-monomer containing at least one carbyne group in an ethereal, polyethereal, or hydrocarbon solvent are presented. A wide variety of arylcarbyne and/or alkylcarbyne monomers and co-monomers can be combined with a source of electrons soluble in an ethereal, polyethereal, or hydrocarbon solvent to form novel polycarbyne polymers. These polycarbyne polymers can be used to form synthetic diamond materials, fibers, and other materials that can withstand extreme conditions.Type: GrantFiled: November 15, 1993Date of Patent: July 25, 1995Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5384078Abstract: A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.Type: GrantFiled: December 15, 1993Date of Patent: January 24, 1995Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5358546Abstract: A novel zerovalent zinc species and an organozinc reagent are disclosed. The zerovalent zinc species is directly produced by reaction of a reducing agent on a zinc salt, preferably Zn(CN).sub.2. The organozinc reagent results from the reaction of the zerovalent zinc species and an organic compound having one or more stable anionic leaving groups. These organozinc reagents include a wide spectrum of functional groups in the organic radical, and are useful in a variety of reactions schemes.Type: GrantFiled: February 4, 1992Date of Patent: October 25, 1994Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5330687Abstract: Calcium-substituted polymeric reagents are provided. These reagents can be prepared via the oxidative addition of a soluble highly reactive calcium species to organic and inorganic polymers containing alkyl, aryl, or alkylaryl pendent groups substituted with halide atoms, cyanide molecules, 1,3-dienes, or any conjugated polyunsaturated system. Preferably, the polymer is a cross-linked p-bromopolystyrene, p-chloropolystyrene, p-fluoropolystyrene, or chloromethylated polystyrene. Preferably, the soluble highly reactive calcium species is prepared from the reduction of Ca(II) salts with an alkali metal arene, such as lithium biphenylide. These calcium-substituted polymeric reagents react with a variety of electrophiles to yield functionalized polymers. Reaction with Cu(I) salts yields calcium-substituted polymeric cuprate reagents, which can react, for example, with acid chlorides to form ketones, alkyl halides containing functionality, and undergo 1,4-conjugate addition with .alpha.,.beta.Type: GrantFiled: July 30, 1992Date of Patent: July 19, 1994Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5231205Abstract: The magnesium complexes of cyclic hydrocarbons, such as 1,2-dimethylenecycloalkanes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, or bromoalkylnitriles serve as a convenient method for synthesizing spirocyclic systems. Significantly, spirocarbocycles prepared by thisThe present invention was made with Government support under Contract No. GM35153 awarded by the National Institute of Health. The Government has certain rights in the invention.Type: GrantFiled: September 23, 1991Date of Patent: July 27, 1993Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5211886Abstract: Calcium-substituted polymeric reagents are provided. These reagents can be prepared via the oxidative addition of a soluble highly reactive calcium species to organic and inorganic polymers containing alkyl, aryl, or alkylaryl pendent groups substituted with halide atoms, cyanide molecules, 1,3-dienes, or any conjugated polyunsaturated system. Preferably, the polymer is a cross-linked p-bromopolystyrene, p-chloropolystyrene, p-fluoropolystyrene, or chloromethylated polystyrene. Preferably, the soluble highly reactive calcium species is prepared from the reduction of Ca(II) salts with an alkali metal arene, such as lithium biphenylide. These calcium-substituted polymeric reagents react with a variety of electrophiles to yield functionalized polymers. Reaction with Cu(I) salts yields calcium-substituted polymeric cuprate reagents, which can react, for example, with acid chlorides to form ketones, alkyl halides containing functionality, and undergo 1,4-conjugate addition with .alpha.,.beta.Type: GrantFiled: August 1, 1991Date of Patent: May 18, 1993Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5211889Abstract: A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.Type: GrantFiled: August 1, 1991Date of Patent: May 18, 1993Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke