Desulfurization of dibenzothiophene by nickel(0) complexes: evidence for electron transfer in oxidative additions
Two equivalents of the complex (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel(0) cleave dibenzothiophene in homogeneous media to form nickel-substituted biphenyl derivatives and nickel sulfide. The cleavage proceeds more readily in tetrahydrofuran (THF) than in benzene solution, and excess amine (e...
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| Veröffentlicht in: | J. Org. Chem.; (United States) 1983-09, Vol.48 (18), p.2963-2968 |
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| creator | EISCH, J. J HALLENBECK, L. E KYOUNG IM HAN |
| description | Two equivalents of the complex (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel(0) cleave dibenzothiophene in homogeneous media to form nickel-substituted biphenyl derivatives and nickel sulfide. The cleavage proceeds more readily in tetrahydrofuran (THF) than in benzene solution, and excess amine (either bipyridyl or pyridine) retards the reaction. Neither biphenylene nor 2-phenylbenzenethiol was a detectable transient in the desulfurization process. The possible fleeting formation of biphenylene was ruled out by a study of the desulfurized products obtained from the 2,8-dimethyl and the 3,7-dimethyl derivatives of dibenzothiophene. A possible role of nickel hydride in some of the C-S bond cleavage is suspected from the observed effects of either acid or lithium aluminum hydride (LiAlH/sub 4/) used in the workup of the reaction mixture. The reaction is not catalytic in nickel when an excess of LiAlH/sub 4/ is used; indicating that Ni(0) cannot be regenerated from NiS under these conditions. The observed cleavage of approx. 50% of the dibenzothiophene by 2 equiv of (2,2'-bipyridyl)(1,5-cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)Ni(C/sub 8/H/sub 12/)) is ascribed to the gradual formation of bis(cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)/sub 2/Ni) which is ineffectual in cleaving dibenzothiophene. Finally, the relative reactivity of the dibenzothiophenes (dibenzothiophene > 2,8-dimethyldibenzothiophene >> 3,7-dimethyldibenzothiophene), the relative effectiveness of amine donors or solvents, and the observed hydrogen abstraction from the solvent are interpreted in terms of an electron-transfer mode of action by the nickel(0) desulfurizing agent. |
| doi_str_mv | 10.1021/jo00166a005 |
| format | Article |
| fullrecord | <record><control><sourceid>pascalfrancis_osti_</sourceid><recordid>TN_cdi_pascalfrancis_primary_9325208</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>9325208</sourcerecordid><originalsourceid>FETCH-LOGICAL-o124t-c8510073e2ebf9b1906b467fca7589d0a37378777837301011e4ae78cafdc87b3</originalsourceid><addsrcrecordid>eNotkM1OwzAQhC0EEqVw4gUsxAEOgbUdxwk3VH6lSlzgHDnOWnVJ7RCnVdunx6jMZecw-nY0hFwyuGPA2f0yALCi0ADyiEyY5JAVFeTHZALAeSZ4IU7JWYxLSJJSTsjPE8Z1Z9eD2-vRBU-Dpa1r0O_DuHChX6BH2uyod-Ybuxu4pSas-g63GB8oblyL3iC1YaDYoRmHRBgH7aPFgbpE27o2cTdIddu6vwfxnJxY3UW8-L9T8vXy_Dl7y-Yfr--zx3kWGM_HzJSSASiBHBtbNayCoskLZY1Wsqxa0EIJVSqlymSAAWOYa1Sl0bY1pWrElFwduCGOro7GjWgWJnifatZSglKQp9D1IdTraHRnU3XjYt0PbqWHXV0JnjYsxS8Fnml1</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Desulfurization of dibenzothiophene by nickel(0) complexes: evidence for electron transfer in oxidative additions</title><source>ACS Publications</source><creator>EISCH, J. J ; HALLENBECK, L. E ; KYOUNG IM HAN</creator><creatorcontrib>EISCH, J. J ; HALLENBECK, L. E ; KYOUNG IM HAN ; State Univ. of New York, Binghamton</creatorcontrib><description>Two equivalents of the complex (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel(0) cleave dibenzothiophene in homogeneous media to form nickel-substituted biphenyl derivatives and nickel sulfide. The cleavage proceeds more readily in tetrahydrofuran (THF) than in benzene solution, and excess amine (either bipyridyl or pyridine) retards the reaction. Neither biphenylene nor 2-phenylbenzenethiol was a detectable transient in the desulfurization process. The possible fleeting formation of biphenylene was ruled out by a study of the desulfurized products obtained from the 2,8-dimethyl and the 3,7-dimethyl derivatives of dibenzothiophene. A possible role of nickel hydride in some of the C-S bond cleavage is suspected from the observed effects of either acid or lithium aluminum hydride (LiAlH/sub 4/) used in the workup of the reaction mixture. The reaction is not catalytic in nickel when an excess of LiAlH/sub 4/ is used; indicating that Ni(0) cannot be regenerated from NiS under these conditions. The observed cleavage of approx. 50% of the dibenzothiophene by 2 equiv of (2,2'-bipyridyl)(1,5-cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)Ni(C/sub 8/H/sub 12/)) is ascribed to the gradual formation of bis(cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)/sub 2/Ni) which is ineffectual in cleaving dibenzothiophene. Finally, the relative reactivity of the dibenzothiophenes (dibenzothiophene > 2,8-dimethyldibenzothiophene >> 3,7-dimethyldibenzothiophene), the relative effectiveness of amine donors or solvents, and the observed hydrogen abstraction from the solvent are interpreted in terms of an electron-transfer mode of action by the nickel(0) desulfurizing agent.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00166a005</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>01 COAL, LIGNITE, AND PEAT ; 010402 - Coal, Lignite, & Peat- Purification & Upgrading ; 02 PETROLEUM ; 020800 - Petroleum- Waste Management ; 400104 - Spectral Procedures- (-1987) ; 400105 - Separation Procedures ; ACETIC ACID ; ADDITIVES ; ALKALI METAL COMPOUNDS ; ALKENES ; ALUMINIUM COMPOUNDS ; ALUMINIUM HYDRIDES ; AROMATICS ; AZINES ; BENZENE ; BIPYRIDINES ; CARBOXYLIC ACIDS ; CHALCOGENIDES ; CHEMICAL REACTION KINETICS ; CHEMICAL REACTION YIELD ; CHEMICAL REACTIONS ; Chemistry ; CHROMATOGRAPHY ; COMPLEXES ; CYCLOALKENES ; DATA ; DESULFURIZATION ; DIENES ; ELECTRON TRANSFER ; Exact sciences and technology ; EXPERIMENTAL DATA ; FORMIC ACID ; FURANS ; GAS CHROMATOGRAPHY ; HETEROCYCLIC COMPOUNDS ; HYDRIDES ; HYDROCARBONS ; HYDROCHLORIC ACID ; HYDROGEN COMPOUNDS ; INFORMATION ; INFRARED SPECTRA ; INORGANIC ACIDS ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; KINETICS ; Kinetics and mechanisms ; LITHIUM COMPOUNDS ; LITHIUM HYDRIDES ; MASS SPECTRA ; MONOCARBOXYLIC ACIDS ; NICKEL COMPLEXES ; NICKEL COMPOUNDS ; NICKEL SULFIDES ; NUMERICAL DATA ; ORGANIC ACIDS ; Organic chemistry ; ORGANIC COMPOUNDS ; ORGANIC NITROGEN COMPOUNDS ; ORGANIC OXYGEN COMPOUNDS ; ORGANIC SOLVENTS ; ORGANIC SULFUR COMPOUNDS ; PHOSPHORIC ACID ; POLYENES ; PYRIDINE ; PYRIDINES ; REACTION INTERMEDIATES ; REACTION KINETICS ; Reactivity and mechanisms ; SEPARATION PROCESSES ; SOLVENTS ; SPECTRA ; STRUCTURAL CHEMICAL ANALYSIS ; SULFIDES ; SULFUR COMPOUNDS ; TETRAHYDROFURAN ; TRANSITION ELEMENT COMPLEXES ; TRANSITION ELEMENT COMPOUNDS ; YIELDS</subject><ispartof>J. Org. Chem.; (United States), 1983-09, Vol.48 (18), p.2963-2968</ispartof><rights>1984 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9325208$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/5507704$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>EISCH, J. J</creatorcontrib><creatorcontrib>HALLENBECK, L. E</creatorcontrib><creatorcontrib>KYOUNG IM HAN</creatorcontrib><creatorcontrib>State Univ. of New York, Binghamton</creatorcontrib><title>Desulfurization of dibenzothiophene by nickel(0) complexes: evidence for electron transfer in oxidative additions</title><title>J. Org. Chem.; (United States)</title><description>Two equivalents of the complex (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel(0) cleave dibenzothiophene in homogeneous media to form nickel-substituted biphenyl derivatives and nickel sulfide. The cleavage proceeds more readily in tetrahydrofuran (THF) than in benzene solution, and excess amine (either bipyridyl or pyridine) retards the reaction. Neither biphenylene nor 2-phenylbenzenethiol was a detectable transient in the desulfurization process. The possible fleeting formation of biphenylene was ruled out by a study of the desulfurized products obtained from the 2,8-dimethyl and the 3,7-dimethyl derivatives of dibenzothiophene. A possible role of nickel hydride in some of the C-S bond cleavage is suspected from the observed effects of either acid or lithium aluminum hydride (LiAlH/sub 4/) used in the workup of the reaction mixture. The reaction is not catalytic in nickel when an excess of LiAlH/sub 4/ is used; indicating that Ni(0) cannot be regenerated from NiS under these conditions. The observed cleavage of approx. 50% of the dibenzothiophene by 2 equiv of (2,2'-bipyridyl)(1,5-cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)Ni(C/sub 8/H/sub 12/)) is ascribed to the gradual formation of bis(cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)/sub 2/Ni) which is ineffectual in cleaving dibenzothiophene. Finally, the relative reactivity of the dibenzothiophenes (dibenzothiophene > 2,8-dimethyldibenzothiophene >> 3,7-dimethyldibenzothiophene), the relative effectiveness of amine donors or solvents, and the observed hydrogen abstraction from the solvent are interpreted in terms of an electron-transfer mode of action by the nickel(0) desulfurizing agent.</description><subject>01 COAL, LIGNITE, AND PEAT</subject><subject>010402 - Coal, Lignite, & Peat- Purification & Upgrading</subject><subject>02 PETROLEUM</subject><subject>020800 - Petroleum- Waste Management</subject><subject>400104 - Spectral Procedures- (-1987)</subject><subject>400105 - Separation Procedures</subject><subject>ACETIC ACID</subject><subject>ADDITIVES</subject><subject>ALKALI METAL COMPOUNDS</subject><subject>ALKENES</subject><subject>ALUMINIUM COMPOUNDS</subject><subject>ALUMINIUM HYDRIDES</subject><subject>AROMATICS</subject><subject>AZINES</subject><subject>BENZENE</subject><subject>BIPYRIDINES</subject><subject>CARBOXYLIC ACIDS</subject><subject>CHALCOGENIDES</subject><subject>CHEMICAL REACTION KINETICS</subject><subject>CHEMICAL REACTION YIELD</subject><subject>CHEMICAL REACTIONS</subject><subject>Chemistry</subject><subject>CHROMATOGRAPHY</subject><subject>COMPLEXES</subject><subject>CYCLOALKENES</subject><subject>DATA</subject><subject>DESULFURIZATION</subject><subject>DIENES</subject><subject>ELECTRON TRANSFER</subject><subject>Exact sciences and technology</subject><subject>EXPERIMENTAL DATA</subject><subject>FORMIC ACID</subject><subject>FURANS</subject><subject>GAS CHROMATOGRAPHY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HYDRIDES</subject><subject>HYDROCARBONS</subject><subject>HYDROCHLORIC ACID</subject><subject>HYDROGEN COMPOUNDS</subject><subject>INFORMATION</subject><subject>INFRARED SPECTRA</subject><subject>INORGANIC ACIDS</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>KINETICS</subject><subject>Kinetics and mechanisms</subject><subject>LITHIUM COMPOUNDS</subject><subject>LITHIUM HYDRIDES</subject><subject>MASS SPECTRA</subject><subject>MONOCARBOXYLIC ACIDS</subject><subject>NICKEL COMPLEXES</subject><subject>NICKEL COMPOUNDS</subject><subject>NICKEL SULFIDES</subject><subject>NUMERICAL DATA</subject><subject>ORGANIC ACIDS</subject><subject>Organic chemistry</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>ORGANIC OXYGEN COMPOUNDS</subject><subject>ORGANIC SOLVENTS</subject><subject>ORGANIC SULFUR COMPOUNDS</subject><subject>PHOSPHORIC ACID</subject><subject>POLYENES</subject><subject>PYRIDINE</subject><subject>PYRIDINES</subject><subject>REACTION INTERMEDIATES</subject><subject>REACTION KINETICS</subject><subject>Reactivity and mechanisms</subject><subject>SEPARATION PROCESSES</subject><subject>SOLVENTS</subject><subject>SPECTRA</subject><subject>STRUCTURAL CHEMICAL ANALYSIS</subject><subject>SULFIDES</subject><subject>SULFUR COMPOUNDS</subject><subject>TETRAHYDROFURAN</subject><subject>TRANSITION ELEMENT COMPLEXES</subject><subject>TRANSITION ELEMENT COMPOUNDS</subject><subject>YIELDS</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><recordid>eNotkM1OwzAQhC0EEqVw4gUsxAEOgbUdxwk3VH6lSlzgHDnOWnVJ7RCnVdunx6jMZecw-nY0hFwyuGPA2f0yALCi0ADyiEyY5JAVFeTHZALAeSZ4IU7JWYxLSJJSTsjPE8Z1Z9eD2-vRBU-Dpa1r0O_DuHChX6BH2uyod-Ybuxu4pSas-g63GB8oblyL3iC1YaDYoRmHRBgH7aPFgbpE27o2cTdIddu6vwfxnJxY3UW8-L9T8vXy_Dl7y-Yfr--zx3kWGM_HzJSSASiBHBtbNayCoskLZY1Wsqxa0EIJVSqlymSAAWOYa1Sl0bY1pWrElFwduCGOro7GjWgWJnifatZSglKQp9D1IdTraHRnU3XjYt0PbqWHXV0JnjYsxS8Fnml1</recordid><startdate>19830909</startdate><enddate>19830909</enddate><creator>EISCH, J. J</creator><creator>HALLENBECK, L. E</creator><creator>KYOUNG IM HAN</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>OTOTI</scope></search><sort><creationdate>19830909</creationdate><title>Desulfurization of dibenzothiophene by nickel(0) complexes: evidence for electron transfer in oxidative additions</title><author>EISCH, J. J ; HALLENBECK, L. E ; KYOUNG IM HAN</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-o124t-c8510073e2ebf9b1906b467fca7589d0a37378777837301011e4ae78cafdc87b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>01 COAL, LIGNITE, AND PEAT</topic><topic>010402 - Coal, Lignite, & Peat- Purification & Upgrading</topic><topic>02 PETROLEUM</topic><topic>020800 - Petroleum- Waste Management</topic><topic>400104 - Spectral Procedures- (-1987)</topic><topic>400105 - Separation Procedures</topic><topic>ACETIC ACID</topic><topic>ADDITIVES</topic><topic>ALKALI METAL COMPOUNDS</topic><topic>ALKENES</topic><topic>ALUMINIUM COMPOUNDS</topic><topic>ALUMINIUM HYDRIDES</topic><topic>AROMATICS</topic><topic>AZINES</topic><topic>BENZENE</topic><topic>BIPYRIDINES</topic><topic>CARBOXYLIC ACIDS</topic><topic>CHALCOGENIDES</topic><topic>CHEMICAL REACTION KINETICS</topic><topic>CHEMICAL REACTION YIELD</topic><topic>CHEMICAL REACTIONS</topic><topic>Chemistry</topic><topic>CHROMATOGRAPHY</topic><topic>COMPLEXES</topic><topic>CYCLOALKENES</topic><topic>DATA</topic><topic>DESULFURIZATION</topic><topic>DIENES</topic><topic>ELECTRON TRANSFER</topic><topic>Exact sciences and technology</topic><topic>EXPERIMENTAL DATA</topic><topic>FORMIC ACID</topic><topic>FURANS</topic><topic>GAS CHROMATOGRAPHY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HYDRIDES</topic><topic>HYDROCARBONS</topic><topic>HYDROCHLORIC ACID</topic><topic>HYDROGEN COMPOUNDS</topic><topic>INFORMATION</topic><topic>INFRARED SPECTRA</topic><topic>INORGANIC ACIDS</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>KINETICS</topic><topic>Kinetics and mechanisms</topic><topic>LITHIUM COMPOUNDS</topic><topic>LITHIUM HYDRIDES</topic><topic>MASS SPECTRA</topic><topic>MONOCARBOXYLIC ACIDS</topic><topic>NICKEL COMPLEXES</topic><topic>NICKEL COMPOUNDS</topic><topic>NICKEL SULFIDES</topic><topic>NUMERICAL DATA</topic><topic>ORGANIC ACIDS</topic><topic>Organic chemistry</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>ORGANIC OXYGEN COMPOUNDS</topic><topic>ORGANIC SOLVENTS</topic><topic>ORGANIC SULFUR COMPOUNDS</topic><topic>PHOSPHORIC ACID</topic><topic>POLYENES</topic><topic>PYRIDINE</topic><topic>PYRIDINES</topic><topic>REACTION INTERMEDIATES</topic><topic>REACTION KINETICS</topic><topic>Reactivity and mechanisms</topic><topic>SEPARATION PROCESSES</topic><topic>SOLVENTS</topic><topic>SPECTRA</topic><topic>STRUCTURAL CHEMICAL ANALYSIS</topic><topic>SULFIDES</topic><topic>SULFUR COMPOUNDS</topic><topic>TETRAHYDROFURAN</topic><topic>TRANSITION ELEMENT COMPLEXES</topic><topic>TRANSITION ELEMENT COMPOUNDS</topic><topic>YIELDS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>EISCH, J. J</creatorcontrib><creatorcontrib>HALLENBECK, L. E</creatorcontrib><creatorcontrib>KYOUNG IM HAN</creatorcontrib><creatorcontrib>State Univ. of New York, Binghamton</creatorcontrib><collection>Pascal-Francis</collection><collection>OSTI.GOV</collection><jtitle>J. Org. Chem.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>EISCH, J. J</au><au>HALLENBECK, L. E</au><au>KYOUNG IM HAN</au><aucorp>State Univ. of New York, Binghamton</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Desulfurization of dibenzothiophene by nickel(0) complexes: evidence for electron transfer in oxidative additions</atitle><jtitle>J. Org. Chem.; (United States)</jtitle><date>1983-09-09</date><risdate>1983</risdate><volume>48</volume><issue>18</issue><spage>2963</spage><epage>2968</epage><pages>2963-2968</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Two equivalents of the complex (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel(0) cleave dibenzothiophene in homogeneous media to form nickel-substituted biphenyl derivatives and nickel sulfide. The cleavage proceeds more readily in tetrahydrofuran (THF) than in benzene solution, and excess amine (either bipyridyl or pyridine) retards the reaction. Neither biphenylene nor 2-phenylbenzenethiol was a detectable transient in the desulfurization process. The possible fleeting formation of biphenylene was ruled out by a study of the desulfurized products obtained from the 2,8-dimethyl and the 3,7-dimethyl derivatives of dibenzothiophene. A possible role of nickel hydride in some of the C-S bond cleavage is suspected from the observed effects of either acid or lithium aluminum hydride (LiAlH/sub 4/) used in the workup of the reaction mixture. The reaction is not catalytic in nickel when an excess of LiAlH/sub 4/ is used; indicating that Ni(0) cannot be regenerated from NiS under these conditions. The observed cleavage of approx. 50% of the dibenzothiophene by 2 equiv of (2,2'-bipyridyl)(1,5-cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)Ni(C/sub 8/H/sub 12/)) is ascribed to the gradual formation of bis(cyclooctadiene) nickel ((C/sub 10/H/sub 8/N/sub 2/)/sub 2/Ni) which is ineffectual in cleaving dibenzothiophene. Finally, the relative reactivity of the dibenzothiophenes (dibenzothiophene > 2,8-dimethyldibenzothiophene >> 3,7-dimethyldibenzothiophene), the relative effectiveness of amine donors or solvents, and the observed hydrogen abstraction from the solvent are interpreted in terms of an electron-transfer mode of action by the nickel(0) desulfurizing agent.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/jo00166a005</doi><tpages>6</tpages></addata></record> |
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| ispartof | J. Org. Chem.; (United States), 1983-09, Vol.48 (18), p.2963-2968 |
| issn | 0022-3263 1520-6904 |
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| recordid | cdi_pascalfrancis_primary_9325208 |
| source | ACS Publications |
| subjects | 01 COAL, LIGNITE, AND PEAT 010402 - Coal, Lignite, & Peat- Purification & Upgrading 02 PETROLEUM 020800 - Petroleum- Waste Management 400104 - Spectral Procedures- (-1987) 400105 - Separation Procedures ACETIC ACID ADDITIVES ALKALI METAL COMPOUNDS ALKENES ALUMINIUM COMPOUNDS ALUMINIUM HYDRIDES AROMATICS AZINES BENZENE BIPYRIDINES CARBOXYLIC ACIDS CHALCOGENIDES CHEMICAL REACTION KINETICS CHEMICAL REACTION YIELD CHEMICAL REACTIONS Chemistry CHROMATOGRAPHY COMPLEXES CYCLOALKENES DATA DESULFURIZATION DIENES ELECTRON TRANSFER Exact sciences and technology EXPERIMENTAL DATA FORMIC ACID FURANS GAS CHROMATOGRAPHY HETEROCYCLIC COMPOUNDS HYDRIDES HYDROCARBONS HYDROCHLORIC ACID HYDROGEN COMPOUNDS INFORMATION INFRARED SPECTRA INORGANIC ACIDS INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY KINETICS Kinetics and mechanisms LITHIUM COMPOUNDS LITHIUM HYDRIDES MASS SPECTRA MONOCARBOXYLIC ACIDS NICKEL COMPLEXES NICKEL COMPOUNDS NICKEL SULFIDES NUMERICAL DATA ORGANIC ACIDS Organic chemistry ORGANIC COMPOUNDS ORGANIC NITROGEN COMPOUNDS ORGANIC OXYGEN COMPOUNDS ORGANIC SOLVENTS ORGANIC SULFUR COMPOUNDS PHOSPHORIC ACID POLYENES PYRIDINE PYRIDINES REACTION INTERMEDIATES REACTION KINETICS Reactivity and mechanisms SEPARATION PROCESSES SOLVENTS SPECTRA STRUCTURAL CHEMICAL ANALYSIS SULFIDES SULFUR COMPOUNDS TETRAHYDROFURAN TRANSITION ELEMENT COMPLEXES TRANSITION ELEMENT COMPOUNDS YIELDS |
| title | Desulfurization of dibenzothiophene by nickel(0) complexes: evidence for electron transfer in oxidative additions |
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