Factors Affecting the Catalytic Epoxidation of Olefins by Iron Porphyrin Complexes and H2O2 in Protic Solvents
The catalytic epoxidation of cyclohexene by iron(III) porphyrin complexes and H2O2 has been investigated in alcohol solvents to understand factors affecting the catalyst activity in protic solvents. The yields of cyclohexene oxide and the FeIII/II reduction potentials of iron porphyrin complexes wer...
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| Veröffentlicht in: | Journal of organic chemistry 2003-10, Vol.68 (20), p.7903-7906 |
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| container_issue | 20 |
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| container_title | Journal of organic chemistry |
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| creator | Nam, Wonwoo Oh, So-Young Sun, Ying Ji Kim, Jinheung Kim, Won-Ki Woo, Seung K Shin, Woonsup |
| description | The catalytic epoxidation of cyclohexene by iron(III) porphyrin complexes and H2O2 has been investigated in alcohol solvents to understand factors affecting the catalyst activity in protic solvents. The yields of cyclohexene oxide and the FeIII/II reduction potentials of iron porphyrin complexes were significantly affected by the protic solvents, and there was a close correlation between the product yields and the reduction potentials of the iron porphyrin catalysts. The role of alcohol solvents was proposed to control the electronic nature of iron porphyrin complexes that determines the catalyst activity in the epoxidation of olefins by H2O2. We have also demonstrated that an electron-deficient iron porphyrin complex can catalyze the epoxidation of olefins by H2O2 under conditions of limiting substrate with high conversion efficiency in a solvent mixture of CH3OH and CH2Cl2. |
| doi_str_mv | 10.1021/jo034493c |
| format | Article |
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The yields of cyclohexene oxide and the FeIII/II reduction potentials of iron porphyrin complexes were significantly affected by the protic solvents, and there was a close correlation between the product yields and the reduction potentials of the iron porphyrin catalysts. The role of alcohol solvents was proposed to control the electronic nature of iron porphyrin complexes that determines the catalyst activity in the epoxidation of olefins by H2O2. We have also demonstrated that an electron-deficient iron porphyrin complex can catalyze the epoxidation of olefins by H2O2 under conditions of limiting substrate with high conversion efficiency in a solvent mixture of CH3OH and CH2Cl2.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034493c</identifier><identifier>PMID: 14510577</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Catalysts: preparations and properties ; Chemistry ; Cyclohexanes - chemistry ; Cyclohexenes ; Epoxy Compounds - chemistry ; Exact sciences and technology ; Ferric Compounds - chemistry ; General and physical chemistry ; Heme - chemistry ; Hydrogen Peroxide - chemistry ; Oxidation-Reduction ; Porphyrins - chemistry ; Solvents ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Journal of organic chemistry, 2003-10, Vol.68 (20), p.7903-7906</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo034493c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo034493c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15168539$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14510577$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nam, Wonwoo</creatorcontrib><creatorcontrib>Oh, So-Young</creatorcontrib><creatorcontrib>Sun, Ying Ji</creatorcontrib><creatorcontrib>Kim, Jinheung</creatorcontrib><creatorcontrib>Kim, Won-Ki</creatorcontrib><creatorcontrib>Woo, Seung K</creatorcontrib><creatorcontrib>Shin, Woonsup</creatorcontrib><title>Factors Affecting the Catalytic Epoxidation of Olefins by Iron Porphyrin Complexes and H2O2 in Protic Solvents</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The catalytic epoxidation of cyclohexene by iron(III) porphyrin complexes and H2O2 has been investigated in alcohol solvents to understand factors affecting the catalyst activity in protic solvents. The yields of cyclohexene oxide and the FeIII/II reduction potentials of iron porphyrin complexes were significantly affected by the protic solvents, and there was a close correlation between the product yields and the reduction potentials of the iron porphyrin catalysts. The role of alcohol solvents was proposed to control the electronic nature of iron porphyrin complexes that determines the catalyst activity in the epoxidation of olefins by H2O2. We have also demonstrated that an electron-deficient iron porphyrin complex can catalyze the epoxidation of olefins by H2O2 under conditions of limiting substrate with high conversion efficiency in a solvent mixture of CH3OH and CH2Cl2.</description><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Cyclohexanes - chemistry</subject><subject>Cyclohexenes</subject><subject>Epoxy Compounds - chemistry</subject><subject>Exact sciences and technology</subject><subject>Ferric Compounds - chemistry</subject><subject>General and physical chemistry</subject><subject>Heme - chemistry</subject><subject>Hydrogen Peroxide - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Porphyrins - chemistry</subject><subject>Solvents</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkUtvEzEUhS0EoqGw4A8gb2A3xY_xzHhZQtNUqpRUDWytO35Qh4k92A5K_j1TNbR3c6VzPp3FOQh9pOSCEka_biPhdS25foVmVDBSNZLUr9GMEMYqzhp-ht7lvCXTCSHeojNaC0pE285QWIAuMWV86ZzVxYdfuDxYPIcCw7F4ja_GePAGio8BR4dXg3U-ZNwf8U2apHVM48Mx-YDncTcO9mAzhmDwkq0YntR1io8p93H4a0PJ79EbB0O2H07_HP1YXG3my-p2dX0zv7ytgBNRKu1sZ6npjJa9qBsKPXSsZoZT2TvZWtsSDlxDy7QgkkJHOtEbKqSUlBjj-Dn68pQ7pvhnb3NRO5-1HQYINu6zakVLOsn5BH46gft-Z40ak99BOqr_DU3A5xMAWcPgEgTt8wsnaNMJLieueuJ8Lvbw7EP6rZqWt0Jt1vfq7vvPzbfFUqi7l1zQWW3jPoWpD0WJelxUPS_K_wG-Po95</recordid><startdate>20031003</startdate><enddate>20031003</enddate><creator>Nam, Wonwoo</creator><creator>Oh, So-Young</creator><creator>Sun, Ying Ji</creator><creator>Kim, Jinheung</creator><creator>Kim, Won-Ki</creator><creator>Woo, Seung K</creator><creator>Shin, Woonsup</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20031003</creationdate><title>Factors Affecting the Catalytic Epoxidation of Olefins by Iron Porphyrin Complexes and H2O2 in Protic Solvents</title><author>Nam, Wonwoo ; Oh, So-Young ; Sun, Ying Ji ; Kim, Jinheung ; Kim, Won-Ki ; Woo, Seung K ; Shin, Woonsup</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a305t-cfe8e1d8dc9b5461aba8242d319bf97ee703a3ca72c5091a8085bd1599910ddf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Cyclohexanes - chemistry</topic><topic>Cyclohexenes</topic><topic>Epoxy Compounds - chemistry</topic><topic>Exact sciences and technology</topic><topic>Ferric Compounds - chemistry</topic><topic>General and physical chemistry</topic><topic>Heme - chemistry</topic><topic>Hydrogen Peroxide - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Porphyrins - chemistry</topic><topic>Solvents</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nam, Wonwoo</creatorcontrib><creatorcontrib>Oh, So-Young</creatorcontrib><creatorcontrib>Sun, Ying Ji</creatorcontrib><creatorcontrib>Kim, Jinheung</creatorcontrib><creatorcontrib>Kim, Won-Ki</creatorcontrib><creatorcontrib>Woo, Seung K</creatorcontrib><creatorcontrib>Shin, Woonsup</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nam, Wonwoo</au><au>Oh, So-Young</au><au>Sun, Ying Ji</au><au>Kim, Jinheung</au><au>Kim, Won-Ki</au><au>Woo, Seung K</au><au>Shin, Woonsup</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Factors Affecting the Catalytic Epoxidation of Olefins by Iron Porphyrin Complexes and H2O2 in Protic Solvents</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-10-03</date><risdate>2003</risdate><volume>68</volume><issue>20</issue><spage>7903</spage><epage>7906</epage><pages>7903-7906</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The catalytic epoxidation of cyclohexene by iron(III) porphyrin complexes and H2O2 has been investigated in alcohol solvents to understand factors affecting the catalyst activity in protic solvents. The yields of cyclohexene oxide and the FeIII/II reduction potentials of iron porphyrin complexes were significantly affected by the protic solvents, and there was a close correlation between the product yields and the reduction potentials of the iron porphyrin catalysts. The role of alcohol solvents was proposed to control the electronic nature of iron porphyrin complexes that determines the catalyst activity in the epoxidation of olefins by H2O2. We have also demonstrated that an electron-deficient iron porphyrin complex can catalyze the epoxidation of olefins by H2O2 under conditions of limiting substrate with high conversion efficiency in a solvent mixture of CH3OH and CH2Cl2.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14510577</pmid><doi>10.1021/jo034493c</doi><tpages>4</tpages></addata></record> |
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| subjects | Catalysis Catalysts: preparations and properties Chemistry Cyclohexanes - chemistry Cyclohexenes Epoxy Compounds - chemistry Exact sciences and technology Ferric Compounds - chemistry General and physical chemistry Heme - chemistry Hydrogen Peroxide - chemistry Oxidation-Reduction Porphyrins - chemistry Solvents Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Factors Affecting the Catalytic Epoxidation of Olefins by Iron Porphyrin Complexes and H2O2 in Protic Solvents |
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