Abstract: The present invention provides processes for the production of chiral compounds in a stereoisomeric excess. The present processes involve reacting a hydrometallated alkene compound with a compound comprising a conjugated-bond system under conditions such that the compounds undergo an asymmetric 1,4- or 1,6-conjugate addition reaction, generating a chiral compound in a stereoisomeric excess. The reaction is performed in the presence of a metal catalyst, which catalyst preferably comprises a non-racemic chiral ligand.

Abstract: Described is a method of synthesizing 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one by reacting 3-(5-ethoxyhept-1-yl)cyclopentene with dichloroketene. The resulting reaction products are reacted with acetic acid and zinc to produce 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-6-one and 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one, which are reacted with trimethylsulfonium iodide to produce 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2?-oxirane] and 4-(5-ethoxyhept-1-yl)spiro-[bicyclo-[3.2.0] heptane-6,2?-oxirane]. Lithium iodide is reacted with 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2?-oxirane] and 4-(5-ethoxyhept-1-yl)spiro-[bicyclo-[3.2.0]heptane-6,2?-oxirane] to produce 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one. A method of synthesizing 6-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-3-one is also described.

Abstract: A phosphine compound represented by general formula (1) wherein R? and R? independently are selected from alkyl, cycloalkyl and 2-furyl radicals, or R? and R? are joined together to form with the phosphorous atom a carbon-phosphorous monocycle including at least 3 carbon atoms or a carbon-phosphorous bicycle; the alkyl radicals, cycloalkyl radicals, and carbon-phosphorous monocycle being unsubstituted or substituted by at least one radical selected from the group of alkyl, cycloalkyl, aryl, alkoxy, and aryloxy radicals; Cps is a partially substituted or completely substituted cyclopentadien-1-yl group, including substitutions resulting in a fused ring system, and wherein a substitution at the 1-position of the cyclopentadien-1-yl group is mandatory when the cyclopentadien-1-yl group is not part of a fused ring system or is part of an indenyl group. These phosphines can be used as ligands in catalytic reactions.

Abstract: The present invention relates to a process for preparing chlorinated or partly chlorinated carbonyl compounds, which comprises reacting unchlorinated or partly chlorinated carbonyl compounds with a chlorinating agent in a jet loop reactor.

Abstract: A method of industrially advantageously producing a cyclopropane monoacetal derivative represented by the formula (III) conveniently and also in a fewer steps by reacting a halogenated unsaturated carbonyl compound represented by the formula (II) with an alcoholate. wherein each symbol is as defined in the specification.

Abstract: The present invention provides a process for the preparation of a bicyclic aminoalcohol which comprises reacting a starting compound, nopinone (I), with XCH2COOR1 wherein X is halogen, and R1 is alkyl, in the presence of an additive and a base to produce a compound (II), converting it to oxime derivative (III), and reducing it with an aluminum hydride

Abstract: An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed. The starting materials used in the synthesis are inexpensive. The principal starting material, (?)-?-Pinene, is on the GRAS list (generally recognized as safe).

Abstract: A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.

Abstract: The invention concerns the use of a solid basic catalyst comprising a hydrotalcite structure wherein part at least of the compensating anions are fluoride anions F? for producing Knoevenagel of Michael condensation reactions. The invention also concerns novel solid basic catalysts comprising a hydrotalcite structure characterized by a Mg/Al molar ratio ranging between 2.5 and 3.8 wherein at least part of the compensating anions are fluoride anions F?, and methods for preparing said novel catalysts.

Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.

Abstract: The present invention relates to a process for the preparation of ?-chloroketones from readily available alkyl esters by the reaction of a sulfoxonium ylide on said alkyl esters to generate a keto sulfoxonium ylide that is in turn treated with anhydrous HCl.

Abstract: In the process for producing a cyclododecanone by isomerizing an epoxycyclododecane-containing starting material in the presence of an isomerization reaction catalyst containing lithium bromide and/or lithium iodide, in order to perform the reaction with high efficiency (high reaction rate) and high selectivity and stably produce a high-purity cyclododecanone in industry while maintaining a high-level reaction rate, the epoxycyclododecane-containing starting material is produced by contacting an epoxycyclododecadiene with hydrogen in the presence of a hydrogen-reduction catalyst and has a content of the hydroxyl group-containing cyclododecane compounds contained in the epoxycyclododecane-containing starting material controlled to 5 mol % or less.

Abstract: Industrially advantageous processes for producing a 2-alkyl-2-cyclopentenone in high yields starting from a 2-(1-hydroxyalkyl)cyclopentanone or a 2-alkylidenecyclopentanone, which are obtainable from a cyclopentanone and a carbonyl compound. A 2-(1-hydroxyalkyl)cyclopentanone represented by the following general formula (1): (wherein R1, R2, R3, R4, R5, R6 and R7 each independently represents hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have one or more substituents or an aromatic group which may have one or more substituents, and each of (1) R6 or R7 with R3 and (2) R6 or R7 with R4 or R5 may be together combined to form a ring which may have a double bond) is subjected to dehydrative isomerization in the presence of a bromine compound and/or an iodine compound.

Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.

Abstract: There is provided a process for producing 2-bromocyclopentanone which process is characterized in that cyclopentanone is reacted with bromine in a biphasic mixture of water and an organic solvent.

Abstract: There is provided a process for producing 2-bromocyclopentanone which process is characterized in that cyclopentanone is reacted with bromine in a biphasic mixture of water and an organic solvent.

Abstract: A process for preparing bicyclic 1,3-diketones of the formula I 1

Abstract: A process for efficiently producing a 2-alkyl-2-cyclopentenone comprising reacting an amine and a hydrogen halide, which are present in a ratio ranging from 1.1:1 to 5:1, with a 2-alkylidene cyclopentanone to carry out an isomerization reaction. A process for producing a jasmonate derivative comprising reacting a 2-alkyl-2-cyclopentenone with a malonic acid diester.

Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.

Abstract: The present invention provides a method for preparing astaxanthin from zeaxanthin. Specifically, the present invention provides a method for said conversion using a halogenating agent with the salt of chloric or bromic acid in an inert solvent.

Abstract: A method of preparing &bgr;-carotene derivatives such as canthaxanthin and astaxanthin is described. The method employs an in situ system to generate hypobromous acid as the oxidizing agent using a salt of sulfite, hydrogen sulfite or bisulfite in combination with a bromate salt. Astaxanthin and canthaxanthin are obtained in good yield with a significantly reduced reaction time.

Abstract: The present invention provides a method for manufacturing 3,4-dihydroxy-3-cyclobutene-1,2-dione represented by the following general formula (III) (usual name: “squaric acid”) through the following reaction processes 1˜4, using a vinyl ether represented by the following general formula (V) and a halogenoacetyl halide represented by the following general formula (VI) as starting materials.

Abstract: The present invention provides a process for producing canthaxanthin by mixing &bgr;-carotene with an alkali metal chlorate or an alkali metal bromate in water and an organic solvent immiscible with water; adding an iodine halide or iodide; and adding a metal iodide whereby the &bgr;-carotene is oxidized to yield canthaxanthin.

Abstract: The invention relates to an improved process for preparing [(3aR,4S,7aS)4-bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminum hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R—Cu, wherein R is and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C1-4 alkyl group, benzyl, or benzyl substituted by at at least one C1-4 alkyl group to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)4-bromooctahydro-7a-methyl-1H-indene-1,5-dione.

Abstract: The invention relates to a process for the halogenation of cyclopropylmethyl ketone with at least one dihalo-triorganophosphorane of the general formula I R3PHal2   (I), in which the radicals R can be the same or different and denote a saturated or unsaturated aliphatic C1-C20 hydrocarbon radical, a phenyl or (C1-C4 alkyl)phenyl radical, which may be optionally substituted by one or two fluorine, chlorine and/or nitro groups, P stands for phosphorus and Hal denotes chlorine, bromine, or iodine, at a temperature of from 800° to 130° C.

Abstract: A widely applicable process for the manufacture of carotenoids by a Wittig reaction comprises carrying out the Wittig reaction in a polar reaction medium in a manner such that neither the reactants nor the thus-manufactured carotenoid are significantly dissolved in the reaction medium. An especially suitable reaction medium is a polar, toxicologically harmless solvent which remains monophasic on the addition of water in an amount up to about 30 vol. % and which permits the triarylphosphine oxide which is formed to dissolve well. Lower alcohols and acetone, as sole solvents or as mixtures with one another and/or with water, are especially suitable as the polar reaction medium. This process permits the use of much more concentrated reaction mixtures, simplifies the regeneration of the solvent and generally the reaction procedure, and avoids toxicologically objectionable solvents such as halogenated hydrocarbons.

Abstract: Described are trimethylcyclohexenylcyclopropyl ketones having the structure: ##STR1## wherein one of the dashed lines is a carbon--carbon double bond and the other of the dashed lines is a carbon--carbon single bond, uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles, and mixtures of same with 3-methyl-1-phenylpentanol-5 and/or butanoylcyclohexane derivatives and/or acetic or propionic acid esters of o-methylphenyl isopropanol.

Abstract: A method for the fluorination of 1,3-diketones and 1,3-ketoesters is disclosed.

Abstract: 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.

Abstract: The invention relates to the use of the known compound 2,6-dichloro-3-fluoro-benzonitrile as active compound in selectively-herbicidal compositions, and to new preparation processes and new intermediates for the preparation of this compound.

Abstract: In the formulae, R.sup.1 represents alkyl; and R.sup.2, R.sup.3 and X independently represent halogen. The present invention relates to a method for producing 3,4-dihydroxy-3-cyclobutene-1, 2-dione of general formula (II) by hydrolyzing 3-alkoxy-2, 2, 4, 4-tetrahalogenocyclobutanone derivative of general formula (I).

Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.

Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.

Abstract: Derivatives of alkyl 3-(substituted or unsubstituted benzylidene)-1-alkyl-2-oxocylopentanecarboxylate of the following formula (I), ##STR1## wherein R.sup.1 and R.sup.2 individually represent a lower alkyl group; X is a halogen atom, a cyano group, an alkyl group, a haloalkyl group, a phenyl group, or a nitro group; and m is an integer of 0 to 5; provided when m is 2 or larger, Xs may be either the same or different. The compounds are useful themselves as an effective ingredient of antifungal compositions, and can be used for intermediates of agriculture chemicals and medicines.

Abstract: The invention concerns pentene derivatives of the general formula (I), in which, independently of each other, R.sup.1 is hydrogen or a methyl group, R.sup.2 and R.sup.3 are hydrogen or an alkyl group with 1 to 5 C-atoms, R.sup.4 is hydrogen or a CHR.sup.5 R.sup.6 group (R.sup.5 and R.sup.6 being hydrogen or an alkyl group with 1 to 6 C-atoms) and X is a CO or CHOH group, with the provision that (a) at least one of the groups R.sup.2 and R.sup.3 is an alkyl group and (b) 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-1-ol is excluded. Such compounds are odoriferous substances with interesting fragrances and high diffusion power.

Abstract: Bisketals of 1,3-cyclobutanedione with monovalent and divalent alcohols as well as processes for their production from 1,3-cyclobutanedione or from 3-acetoxy-2-cyclobuten-1-one contained in the distillation residues of the diketene production. The bisketals are suitable intermediate products for the production of squaric acid, for the production and/or purification of 1,3-cyclobutanedione, or as a stable form for storage or substitute for this unstable dione.

Abstract: The present invention provides a method for producing optically active 3-substituted-2-norbornanones which are useful as starting materials for several kinds of physiologically active materials, and to their intermediates, optically active 2-hydroxy-2-norbornanecarboxylic acid and to a method for producing these intermediates.

Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.

Abstract: Pyrethrolone of the formula [II], ##STR1## is produced by reacting a cyclopentenolone derivative of the formula [I], ##STR2## with zinc in an aqueous alcohol solvent. And the cyclopentenolone derivative of the formula [I] is produced by reacting a propargylcyclopentenolone derivative of the formula [III], ##STR3## with vinyl halide in the presence of a palladium catalyst, a copper catalyst and a tertiary amine. These processes permit easy production of pyrethrolone of the formula [II] and an intermediate compound of the formula [I] for the production of the pyrethrolone.

Abstract: Provided is a process which comprises conducting the ring-closure of pseudoirone in the presence of chlorosulfonic acid, which is inexpensive, to obtain in a high yield the .alpha.-cis form of irone, which has nearly the same fragrance as that of natural irones.

Abstract: This invention concerns a process for preparing fluoroalkyl substituted olefins, fluorinated ketones and fluorinated aromatic compounds by the catalyzed reaction of fluoroalkylsilanes with selected fluorinated olefins, acyl fluorides and fluorinated aromatic compounds, respectively.

Abstract: A process for the production of squaric acid by halogenation either of pure 3-acetoxy-2-cyclobuten-1-one or of a distillation residue of diketene production containing 3-acetoxy-2-cyclobuten-1-one to a cyclobutenone of formula: ##STR1## and then hydrolysis of these cyclobutenones to squaric acid. The halogenated cyclobutenones are intermediate products in the process.

Abstract: 3-Hydroxy-2-cyclobuten-1-one salts of the general formula: ##STR1## wherein R is an ammonium group of the general formula: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different in meaning and each is a hydrogen atom, a lower alkyl group or a cycloalkyl group or R is an alkali metal atom. The salts according for formula I are obtained by the reaction of pure 3-acetoxy-2-cyclobuten-1-one, or 1,3-cyclobutanedione or a distillation residue of the diketene production containing 3-acetoxy-2-cyclobuten-1-one, with a base. The base can be an amine of the general formula: ##STR3## wherein R.sub.1, R.sub.2, and R.sub.3 have the above-mentioned meaning, or an alkali metal alcoholate or an alkali metal hydroxide. The salts according to formula I are suitable for the production of squaric acid, by their being halogenated in a first step and then being hydrolyzed to squaric acid in a second step.

Abstract: 2,3,5-trisubstituted-2-cyclopentenones or 2,3-disubstituted-2-cyclopentenones (such as cis-jasmone) are prepared by contacting a 3-chloro-3,4-disubstituted-4-pentene-2-one with a strong base. Methods of preparing the reactants are also disclosed.

Abstract: A method for the manufacture of the four geometric isomers of 4(2-butenylidene)-3,5,5-trimethyl-2-cyclohexen-1-one is provided. The process comprises pyrolyzing a compound of the formula ##STR1## wherein R represents lower-alkyl-oxycarbonyl, aryl-oxycarbonyl, or, preferably, lower-alkanoyl, benzoyl or substituted benzoyl.

Abstract: A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.

Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.

Abstract: Azulene derivatives of the following formula ##STR1## wherein R.sup.1 stands for an alkyl group of 1 to 3 carbon atoms, R.sup.2 stands for an alkyl group of 1 to 3 carbon atoms, and R.sup.3 is at the 5- or 6-position and stands for an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 9 carbon atoms or an aralkyl group of 7 to 10 carbon atoms; have antihyperlipidemic activity. Many of the compounds are also novel per se.

Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts and a proton source. The reaction--which is conducted, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substitutes are a perfluoroalkyl group and a hydroxyl group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.

Abstract: A novel process for producing a .beta.-dihalogenoethenylcyclopropane derivative of the formula, ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl group, R.sub.3 is a hydrogen atom, lower alkyl, acyl, carboxyl or alkoxycarbonyl group and R is a hydrogen atom or a lower alkyl group and each of Y.sub.1 and Y.sub.2 is a fluorine, chlorine or bromine atom respectively, which is an acidic moiety of the useful synthetic insecticides of the pyrethrin type, which process comprises a combination of a series of sequential steps starting from alkyl 3-butenyl ketone derivative of the formula (I), which may be shown according to the following reaction scheme: ##STR2## According to this process, objective compound of the formula (VI) having any cis/trans ratio can be produced by selecting the reaction condition of the Stages II-1, II-2, and IV-2.