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    Process for the production of cyclic organic compounds
    3.
    发明授权
    Process for the production of cyclic organic compounds 失效
    环状有机化合物的制备方法

    公开(公告)号：US3215712A

    公开(公告)日：1965-11-02

    申请号：US9746061

    申请日：1961-03-22

    Applicant: UNION CARBIDE CORP

    Inventor： HUBEL KARL W

    IPC: C07C1/32 ,  C07C45/00 ,  C07C46/00 ,  C07C50/02 ,  C07C50/06 ,  C07F7/08 ,  C07F17/00 ,  C10L1/30 ,  C23C16/16

    CPC classification number: C23C16/16 ,  C07C1/325 ,  C07C45/00 ,  C07C46/00 ,  C07C50/02 ,  C07C50/06 ,  C07F7/0818 ,  C07F7/0827 ,  C07F17/00 ,  C10L1/30 ,  C10L1/305 ,  Y10S585/931 ,  C07C15/02

    Abstract: The invention comprises the product of reacting under neutral non-aqueous conditions a transition metal carbonyl or a derivative thereof with an acetylene compound the product having the formula where M is a transition metal, N is a carbonyl group or a substituted carbonyl group, R1 and R11 each represent hydrogen or an organic group or substituted derivatives thereof or an organo substituted hydride group, C2 represents direct carbon to carbon bonding, x is an integer from 1 to 3, y is an integer from 2 to 12 and z is an integer from 1 to 5. M may be iron, znickel, ruthenium, rhodium, palladium, osmium iridium, manganese, rhenium, chromium, molybdenum or tungsten. The triple bond in the acetylene compound is converted into a double or single bond. If desired, the transition metal carbonyl may be prepared in situ from the metal and carbon monoxide; alternatively, a metal salt and a reducing agent may be used. The acetylene compound may be substituted by an organic group such as an alkyl, alkenyl, alkynyl, cycloaliphatic, aryl or alkylaryl group or a functional group such as -COH, -CN, -halogen, -OH, -NR2, -COOR wherein R is hydrogen, an aliphatic or aromatic radical or a hydrocarbon group substituted by such a functional group. The products may be separated by chromatography or by fractional crystallisation. From 2.5 to 6.0 moles of acetylenic compound may be used per mol of metal carbonyl. The temperature of reaction varies from room temperature up to 300 DEG C. If desired, the carbonyl groups on the metal may be partially substituted by radicals such as nitrosyl, substituted isonitrile, substituted phosphines, substituted arsines, substituted stibines and their halides and fully substituted aromatic systems. Complicated ring systems may be formed by heating the compounds of the invention, thus 1,3,5-triphenylbenzene is obtained by heating Fe2(CO)6(C6H5.C2H)3 or Fe(CO)4(C6H5.C2H)3 to about 170 DEG C. Heating Fe(CO)4(C6H5.C2.C6H5)2 to about 200 DEG C. yields tetraphenylcyclopentadienone, and heating Fe(CO)2(CH3OOC.C2.COOCH3)3 to 180 DEG C. yields the hexamethyl ester of mellitic acid.ALSO:Complexes obtained by heating a transition metal carbonyl and an acetylenic compound (see Group IV(b)) may be decomposed thermally to produce metal mirrors and films. Thus glass cloth may be coated with iron by heating the cloth in a sealed tube containing Fe2(CO)6-(C6H5.C2.C6H5) 2.

    Five membered zirconium,boron,thallium and gold heterocyclic compounds
    6.
    发明授权
    Five membered zirconium,boron,thallium and gold heterocyclic compounds 失效
    五成分锆，硼，铊和金杂环化合物

    公开(公告)号：US3426052A

    公开(公告)日：1969-02-04

    申请号：US3426052D

    申请日：1960-06-15

    Applicant: UNION CARBIDE CORP

    Inventor： HUBEL KARL W ,  BRAYE EMILE H

    IPC: C07C1/32 ,  C07C17/26 ,  C07C45/00 ,  C07C45/27 ,  C07C45/30 ,  C07C46/00 ,  C07C49/796 ,  C07C50/06 ,  C07C335/32 ,  C07D207/32 ,  C07D207/323 ,  C07D307/36 ,  C07D309/38 ,  C07D333/08 ,  C07F3/00 ,  C07F3/06 ,  C07F5/00 ,  C07F5/06 ,  C07F7/00 ,  C07F7/08 ,  C07F9/6568 ,  C07F9/70 ,  C07F9/90 ,  C07F9/94 ,  C07F15/02 ,  C07F17/00 ,  C07F1/12 ,  C07F5/02

    CPC classification number: C07D207/323 ,  C07C1/325 ,  C07C335/32 ,  C07D307/36 ,  C07D309/38 ,  C07D333/08 ,  C07F3/00 ,  C07F3/06 ,  C07F5/00 ,  C07F5/069 ,  C07F7/00 ,  C07F7/0807 ,  C07F9/65683 ,  C07F9/65685 ,  C07F9/706 ,  C07F9/906 ,  C07F9/94 ,  C07F15/02 ,  C07F17/00

    Abstract: Organic compounds comprising one or more R1C2R11 groups wherein R1 and R11 are the same or different and each represents hydrogen, halogen or an alkyl, aryl, cycloaliphatic, alkoxy or carboalkoxy group or a silyl group (see Division C3) and C2 represents a carbon-to-carbon bonding are prepared by reacting an organometallic complex, as defined below, with a hydrogenating agent, a halogenating agent, an oxidising agent, an alkylating agent, an alkyne, an element of Group VIa of the Periodic Table (as quoted on pages 392 and 393 of The Handbook of Chemistry and Physics, 37th edition, published by the Chemical Rubber Publishing Co.) or a reactive compound as defined below. The term "organo-metallic complex" is defined as a complex having the general formula Mx(CO)y (R1C2R11)z wherein M represents iron, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, manganese, rhenium, chromium, molybdenum, or tungsten, CO represents a carbonyl group bonded to the said metal, to the R1C2R11 group, or to both, R1C2R11 is a group as defined above, x is from 1 to 4, y is from 1 to 10, z is from 1 to 6, prepared by the method described and claimed in Specification 885,514. The expression "reactive compound" is defined as a compound selected from nitrosyl chloride, nitrosobenzene, N,N-dichloro-p-toluenesulphonamide, phenyldichlorophosphine, benzyldichlorophosphine, benzyldibromophosphine, phenyldichloroarsine, polysulphides, mono- and di-halogeno-phosphines, -arsines or -stibines, polyselenides, sulphur dioxide, potassium selenocyanide (KSeCN), sulphur dichloride and triphenylphosphine selenide. Complexes in which the carbonyl group bonded to the metal is partially replaced by a nitronyl, a substituted stibine, a substituted arsine, or a substituted phosphine may also be used. Numerous suitable complexes and reactants of the above types are specified, some of the reactants falling into more than one of the specified classes. Many types of compound which may be obtained by the process of the invention are specified including ketones, phenols, esters, ethers, sulphonamides, halogen compounds and heterocyclic compounds containing nitrogen, phosphorus, arsenic, oxygen, sulphur or selenium as the hetero-atom. Some of the compounds produced are stated to be novel, in particular, 2,5-dimethyl-3,4-diphenylthiophene, tetraphenylselenophene, pentaphenylphosphole, P-benzyl-tetraphenylphosphole, pentaphenylarsole, tetraethylselenophene, tetraphenyl-g -pyrone tetraphenyl - 1 - thia - 4 - pyrone, tetraphenyl - 1 - selena-4-pyrone, 1,4-bis-(p-toluene-sulphonamido) 1, 2, 3, 4-tetraphenylbutadiene, 1,4-bis-(p-toluene-sulphonamido) 1, 4-dimethoxybutane, 1, 2, 3, 4-tetraphenyl-5, 6-bis-(p-chlorophenyl)-benzene and compounds of the formulae: and wherein the groups R may be identical or different and may take any of the values given above for R1 and R11, and wherein X represents phosphorus or arsenic. Examples are given. The examples also disclose the following reactions: (6) the isomerisation of cis-dibenzoyl-stilbene to the trans-isomer; (17) conversion of pentaphenylphosphole to the corresponding P-oxide, -sulphide or -selenide; (19) reaction of benzyldichlorophosphine with 1,4-dilithio-1,2,3,4-tetraphenylbutadiene to give P-benzyl-tetraphenyl-phosphole; (20) reaction of phenyldichloroarsine with 1,4-dilithio-1,2,3,4-tetraphenylbutadiene to give pentaphenylarsole; (23) heating hexyne-3 with sulphur to give tetraethylthiophene; (25) heating hexyne-3 with potassium polyselenide to give tetraethylselenophene. The compounds of formula (1) above may be converted to the corresponding phosphole or arsole oxides, sulphides or selenides or may undergo Diels-Alder reactions, for example with maleic anhydride. The compounds of formula (2) above, or the corresponding compounds in which the hetero-atom is a Group VIa (as defined above) other than selenium, may be reacted with ammonia to give g -pyridones. Some of the products of the process of the invention are stated to be useful as insecticides, fluorescent materials, chelating agents and polar solvents, and in the production of polymers. The Provisional Specification refers also to the use of complexes of the above type in which the metal is cobalt.ALSO:Organo-silicon compounds are prepared by reacting an organo-metallic complex, as defined below, with a silicon compound such as phenyltrimethylsilyl acetylene and bis-(trimethylsilyl) acetylene. The term "organo-metallic complex" is defined as a complex having the general formula Mx(CO)y(R1C2R11)z wherein M represents iron, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, manganese, rhenium, chromium, molybdenum or tungsten, CO represents a carbonyl group bonded to the said metal, to the R1C2R11 group, or to both, R1C2R11 is a hydrocarbon group, x is from 1 to 4, y is from 1 to 10, z is from 1 to 6, prepared by the method described and claimed in Specification 885,514. Products of the formulae: wherein X represents phosphorus or arsenic and the groups R may be identical or different and may be a silyl group, are stated to be novel. Examples 19 and 20 of the Provisional Specification describe the preparation of 1,3-bis-(trimethylsilyl) - 2, 4, 5, 6 - tetraphenylbenzene, 1, 3, 5 - tris - (trimethylsilyl) - 2, 4, 6 - triphenylbenzene, trimethylsilyl - triphenyl - cyclopentadienones, 2, 5 - bis - (trimethylsilyl) - 3, 4-diphenylcyclopentadienone and 2, 4 - bis - (trimethylsilyl) - 3, 5 - diphenylcyclopentadienone, using complexes of the above type in which the metal is cobalt.ALSO:Hydrocarbons comprising one or more R1C2R11 groups wherein R1 and R11 ar the same or different and each represents hydrogen or an alkyl, aryl or cycloaliphatic group and C2 represents a carbon-to-carbon bonding are prepared by reacting an organo-metallic complex, as defined below, with a hydrogenating agent or an alkyne. The term "organo-metallic complex" comprises complexes having the general formula Mx(CO)y(R1C2R11)z wherein M represents iron, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, manganese, rhenium, chromium, molybdenum or tungsten, CO represents a carbonyl group bonded to the said metal, to the R1C2R11 group, or to both, R1C2R11 is a group as defined above, x is from 1 to 4, y is from 1 to 10, z is from 1 to 6, prepared by the method described and claimed in Specification 885,514. Complexes in which the carbonyl group bonded to the metal is partially replaced by a nitrosyl, a substituted stibine, a substituted arsine, or a substituted phosphine may also be used. Numerous suitable complexes and reactants of the above types are specified. Examples describe the preparation of 1, 2, 3, 4-tetraphenyl-butadiene, 1,2,3,4-tetraphenylbut - 1 - ene, 1,2,3,4 - tetraphenylbutane, 1,2,3,4 - tetraphenylbutane, dibenzyl, stilbene, and an unidentified compound of the formula (C6H5.C2.C6H5)3H2, from complexes containing tetraphenylacetylene by reduction with lithium aluminium hydride or sodium and ethanol in liquid ammonia and of 1,2,3,4-tetraphenylbenzene and hexaphenylbenzene by reacting diphenyl-acetylene with Fe(CO)4(C6H5C2H)2. The Provisional Specification also refers to the use of complexes of the above type in which the metal is cobalt.

    Process for the preparation of heteroatom containing organic compounds
    7.
    发明授权
    Process for the preparation of heteroatom containing organic compounds 失效

    公开(公告)号：US3280017A

    公开(公告)日：1966-10-18

    申请号：US1880560

    申请日：1960-03-31

    Applicant: UNION CARBIDE CORP

    Inventor： HUBEL KARL W ,  HENRI BRAYE EMILE

    IPC: C07C1/32 ,  C07C17/26 ,  C07C45/00 ,  C07C45/27 ,  C07C45/30 ,  C07C46/00 ,  C07C49/796 ,  C07C50/06 ,  C07C335/32 ,  C07D207/32 ,  C07D207/323 ,  C07D307/36 ,  C07D309/38 ,  C07D333/08 ,  C07F3/00 ,  C07F3/06 ,  C07F5/00 ,  C07F5/06 ,  C07F7/00 ,  C07F7/08 ,  C07F9/6568 ,  C07F9/70 ,  C07F9/90 ,  C07F9/94 ,  C07F15/02 ,  C07F17/00

    CPC classification number: C07D207/323 ,  C07C1/325 ,  C07C335/32 ,  C07D307/36 ,  C07D309/38 ,  C07D333/08 ,  C07F3/00 ,  C07F3/06 ,  C07F5/00 ,  C07F5/069 ,  C07F7/00 ,  C07F7/0807 ,  C07F9/65683 ,  C07F9/65685 ,  C07F9/706 ,  C07F9/906 ,  C07F9/94 ,  C07F15/02 ,  C07F17/00

    Abstract: Organic compounds comprising one or more R1C2R11 groups wherein R1 and R11 are the same or different and each represents hydrogen, halogen or an alkyl, aryl, cycloaliphatic, alkoxy or carboalkoxy group or a silyl group (see Division C3) and C2 represents a carbon-to-carbon bonding are prepared by reacting an organometallic complex, as defined below, with a hydrogenating agent, a halogenating agent, an oxidising agent, an alkylating agent, an alkyne, an element of Group VIa of the Periodic Table (as quoted on pages 392 and 393 of The Handbook of Chemistry and Physics, 37th edition, published by the Chemical Rubber Publishing Co.) or a reactive compound as defined below. The term "organo-metallic complex" is defined as a complex having the general formula Mx(CO)y (R1C2R11)z wherein M represents iron, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, manganese, rhenium, chromium, molybdenum, or tungsten, CO represents a carbonyl group bonded to the said metal, to the R1C2R11 group, or to both, R1C2R11 is a group as defined above, x is from 1 to 4, y is from 1 to 10, z is from 1 to 6, prepared by the method described and claimed in Specification 885,514. The expression "reactive compound" is defined as a compound selected from nitrosyl chloride, nitrosobenzene, N,N-dichloro-p-toluenesulphonamide, phenyldichlorophosphine, benzyldichlorophosphine, benzyldibromophosphine, phenyldichloroarsine, polysulphides, mono- and di-halogeno-phosphines, -arsines or -stibines, polyselenides, sulphur dioxide, potassium selenocyanide (KSeCN), sulphur dichloride and triphenylphosphine selenide. Complexes in which the carbonyl group bonded to the metal is partially replaced by a nitronyl, a substituted stibine, a substituted arsine, or a substituted phosphine may also be used. Numerous suitable complexes and reactants of the above types are specified, some of the reactants falling into more than one of the specified classes. Many types of compound which may be obtained by the process of the invention are specified including ketones, phenols, esters, ethers, sulphonamides, halogen compounds and heterocyclic compounds containing nitrogen, phosphorus, arsenic, oxygen, sulphur or selenium as the hetero-atom. Some of the compounds produced are stated to be novel, in particular, 2,5-dimethyl-3,4-diphenylthiophene, tetraphenylselenophene, pentaphenylphosphole, P-benzyl-tetraphenylphosphole, pentaphenylarsole, tetraethylselenophene, tetraphenyl-g -pyrone tetraphenyl - 1 - thia - 4 - pyrone, tetraphenyl - 1 - selena-4-pyrone, 1,4-bis-(p-toluene-sulphonamido) 1, 2, 3, 4-tetraphenylbutadiene, 1,4-bis-(p-toluene-sulphonamido) 1, 4-dimethoxybutane, 1, 2, 3, 4-tetraphenyl-5, 6-bis-(p-chlorophenyl)-benzene and compounds of the formulae: and wherein the groups R may be identical or different and may take any of the values given above for R1 and R11, and wherein X represents phosphorus or arsenic. Examples are given. The examples also disclose the following reactions: (6) the isomerisation of cis-dibenzoyl-stilbene to the trans-isomer; (17) conversion of pentaphenylphosphole to the corresponding P-oxide, -sulphide or -selenide; (19) reaction of benzyldichlorophosphine with 1,4-dilithio-1,2,3,4-tetraphenylbutadiene to give P-benzyl-tetraphenyl-phosphole; (20) reaction of phenyldichloroarsine with 1,4-dilithio-1,2,3,4-tetraphenylbutadiene to give pentaphenylarsole; (23) heating hexyne-3 with sulphur to give tetraethylthiophene; (25) heating hexyne-3 with potassium polyselenide to give tetraethylselenophene. The compounds of formula (1) above may be converted to the corresponding phosphole or arsole oxides, sulphides or selenides or may undergo Diels-Alder reactions, for example with maleic anhydride. The compounds of formula (2) above, or the corresponding compounds in which the hetero-atom is a Group VIa (as defined above) other than selenium, may be reacted with ammonia to give g -pyridones. Some of the products of the process of the invention are stated to be useful as insecticides, fluorescent materials, chelating agents and polar solvents, and in the production of polymers. The Provisional Specification refers also to the use of complexes of the above type in which the metal is cobalt.ALSO:Organo-silicon compounds are prepared by reacting an organo-metallic complex, as defined below, with a silicon compound such as phenyltrimethylsilyl acetylene and bis-(trimethylsilyl) acetylene. The term "organo-metallic complex" is defined as a complex having the general formula Mx(CO)y(R1C2R11)z wherein M represents iron, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, manganese, rhenium, chromium, molybdenum or tungsten, CO represents a carbonyl group bonded to the said metal, to the R1C2R11 group, or to both, R1C2R11 is a hydrocarbon group, x is from 1 to 4, y is from 1 to 10, z is from 1 to 6, prepared by the method described and claimed in Specification 885,514. Products of the formulae: wherein X represents phosphorus or arsenic and the groups R may be identical or different and may be a silyl group, are stated to be novel. Examples 19 and 20 of the Provisional Specification describe the preparation of 1,3-bis-(trimethylsilyl) - 2, 4, 5, 6 - tetraphenylbenzene, 1, 3, 5 - tris - (trimethylsilyl) - 2, 4, 6 - triphenylbenzene, trimethylsilyl - triphenyl - cyclopentadienones, 2, 5 - bis - (trimethylsilyl) - 3, 4-diphenylcyclopentadienone and 2, 4 - bis - (trimethylsilyl) - 3, 5 - diphenylcyclopentadienone, using complexes of the above type in which the metal is cobalt.ALSO:Hydrocarbons comprising one or more R1C2R11 groups wherein R1 and R11 ar the same or different and each represents hydrogen or an alkyl, aryl or cycloaliphatic group and C2 represents a carbon-to-carbon bonding are prepared by reacting an organo-metallic complex, as defined below, with a hydrogenating agent or an alkyne. The term "organo-metallic complex" comprises complexes having the general formula Mx(CO)y(R1C2R11)z wherein M represents iron, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, manganese, rhenium, chromium, molybdenum or tungsten, CO represents a carbonyl group bonded to the said metal, to the R1C2R11 group, or to both, R1C2R11 is a group as defined above, x is from 1 to 4, y is from 1 to 10, z is from 1 to 6, prepared by the method described and claimed in Specification 885,514. Complexes in which the carbonyl group bonded to the metal is partially replaced by a nitrosyl, a substituted stibine, a substituted arsine, or a substituted phosphine may also be used. Numerous suitable complexes and reactants of the above types are specified. Examples describe the preparation of 1, 2, 3, 4-tetraphenyl-butadiene, 1,2,3,4-tetraphenylbut - 1 - ene, 1,2,3,4 - tetraphenylbutane, 1,2,3,4 - tetraphenylbutane, dibenzyl, stilbene, and an unidentified compound of the formula (C6H5.C2.C6H5)3H2, from complexes containing tetraphenylacetylene by reduction with lithium aluminium hydride or sodium and ethanol in liquid ammonia and of 1,2,3,4-tetraphenylbenzene and hexaphenylbenzene by reacting diphenyl-acetylene with Fe(CO)4(C6H5C2H)2. The Provisional Specification also refers to the use of complexes of the above type in which the metal is cobalt.

    Organo-metallo-carbonyl complexes prepared by the reaction of acetylene with a metalcarbonyl
    8.
    发明授权
    Organo-metallo-carbonyl complexes prepared by the reaction of acetylene with a metalcarbonyl 失效
    通过乙炔与金属羰基反应制备的有机金属羰基络合物

    公开(公告)号：US3188335A

    公开(公告)日：1965-06-08

    申请号：US21910262

    申请日：1962-08-24

    Applicant: UNION CARBIDE CORP

    Inventor： HUBEL KARL W

    IPC: C07C1/32 ,  C07C45/00 ,  C07C46/00 ,  C07C50/02 ,  C07C50/06 ,  C07F7/08 ,  C07F17/00 ,  C10L1/30 ,  C23C16/16

    CPC classification number: C23C16/16 ,  C07C1/325 ,  C07C45/00 ,  C07C46/00 ,  C07C50/02 ,  C07C50/06 ,  C07F7/0818 ,  C07F7/0827 ,  C07F17/00 ,  C10L1/30 ,  C10L1/305 ,  Y10S585/931 ,  C07C15/02

    Abstract: The invention comprises the product of reacting under neutral non-aqueous conditions a transition metal carbonyl or a derivative thereof with an acetylene compound the product having the formula where M is a transition metal, N is a carbonyl group or a substituted carbonyl group, R1 and R11 each represent hydrogen or an organic group or substituted derivatives thereof or an organo substituted hydride group, C2 represents direct carbon to carbon bonding, x is an integer from 1 to 3, y is an integer from 2 to 12 and z is an integer from 1 to 5. M may be iron, znickel, ruthenium, rhodium, palladium, osmium iridium, manganese, rhenium, chromium, molybdenum or tungsten. The triple bond in the acetylene compound is converted into a double or single bond. If desired, the transition metal carbonyl may be prepared in situ from the metal and carbon monoxide; alternatively, a metal salt and a reducing agent may be used. The acetylene compound may be substituted by an organic group such as an alkyl, alkenyl, alkynyl, cycloaliphatic, aryl or alkylaryl group or a functional group such as -COH, -CN, -halogen, -OH, -NR2, -COOR wherein R is hydrogen, an aliphatic or aromatic radical or a hydrocarbon group substituted by such a functional group. The products may be separated by chromatography or by fractional crystallisation. From 2.5 to 6.0 moles of acetylenic compound may be used per mol of metal carbonyl. The temperature of reaction varies from room temperature up to 300 DEG C. If desired, the carbonyl groups on the metal may be partially substituted by radicals such as nitrosyl, substituted isonitrile, substituted phosphines, substituted arsines, substituted stibines and their halides and fully substituted aromatic systems. Complicated ring systems may be formed by heating the compounds of the invention, thus 1,3,5-triphenylbenzene is obtained by heating Fe2(CO)6(C6H5.C2H)3 or Fe(CO)4(C6H5.C2H)3 to about 170 DEG C. Heating Fe(CO)4(C6H5.C2.C6H5)2 to about 200 DEG C. yields tetraphenylcyclopentadienone, and heating Fe(CO)2(CH3OOC.C2.COOCH3)3 to 180 DEG C. yields the hexamethyl ester of mellitic acid.ALSO:Complexes obtained by heating a transition metal carbonyl and an acetylenic compound (see Group IV(b)) may be decomposed thermally to produce metal mirrors and films. Thus glass cloth may be coated with iron by heating the cloth in a sealed tube containing Fe2(CO)6-(C6H5.C2.C6H5) 2.

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