Simultaneous capture of two distinct radical ion intermediates generated from the EDA complexes of three-membered compounds with TCNE by photoexcitation and in the dark
Irradiation of the electron donor-acceptor (EDA) complexes of 2,2-diaryl-1-methylenecyclopropanes, 1,1,2,2-tetraarylcyclopropanes, 2,3-diaryloxiranes, or 2,3-diarylaziridines with tetracyanoethylene (TCNE) under aerated conditions involved oxygenation and/or the (3 + 2) cycloaddition with TCNE. The...
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| Veröffentlicht in: | J. Am. Chem. Soc.; (United States) 1987-04, Vol.109 (9), p.2780-2788 |
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| container_title | J. Am. Chem. Soc.; (United States) |
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| creator | MIYASHI, T KAMATA, M MUKAI, T |
| description | Irradiation of the electron donor-acceptor (EDA) complexes of 2,2-diaryl-1-methylenecyclopropanes, 1,1,2,2-tetraarylcyclopropanes, 2,3-diaryloxiranes, or 2,3-diarylaziridines with tetracyanoethylene (TCNE) under aerated conditions involved oxygenation and/or the (3 + 2) cycloaddition with TCNE. The same oxygenation took place in the dark when the EDA complexes of 2,2-diaryl-1-methylenecyclopropanes or 1,1,2,2-tetraarylcyclopropanes with TCNE were simply stirred in oxygen-saturated solvents. Oxygenation occurred much more efficiently as the solvent polarity and the electron-donative nature of donor substrates increased. 1,2,4,5-Tetramethoxybenzene (TMB) used as a quencher efficiently suppressed oxygenation but not the (3 + 2) cycloaddition at all. Oxygenation occurs through the solvent-separated radical cations diffused from the photogenerated geminate radical ion pairs, whereas the cage coupling of the radical ion pairs involves the (3 + 2) cycloaddition with TCNE. |
| doi_str_mv | 10.1021/ja00243a035 |
| format | Article |
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The same oxygenation took place in the dark when the EDA complexes of 2,2-diaryl-1-methylenecyclopropanes or 1,1,2,2-tetraarylcyclopropanes with TCNE were simply stirred in oxygen-saturated solvents. Oxygenation occurred much more efficiently as the solvent polarity and the electron-donative nature of donor substrates increased. 1,2,4,5-Tetramethoxybenzene (TMB) used as a quencher efficiently suppressed oxygenation but not the (3 + 2) cycloaddition at all. Oxygenation occurs through the solvent-separated radical cations diffused from the photogenerated geminate radical ion pairs, whereas the cage coupling of the radical ion pairs involves the (3 + 2) cycloaddition with TCNE.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja00243a035</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>ALKANES ; ALKENES ; CATIONS ; CHARGED PARTICLES ; CHEMICAL REACTIONS ; CHEMISTRY ; CYCLOALKANES ; DATA ; DIFFUSION ; ELECTRON TRANSFER ; ELEMENTS ; EPOXIDES ; Exact sciences and technology ; EXPERIMENTAL DATA ; General and physical chemistry ; HYDROCARBONS ; INFORMATION ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; IONS ; NONMETALS ; NUMERICAL DATA ; ORGANIC COMPOUNDS ; ORGANIC NITROGEN COMPOUNDS ; ORGANIC OXYGEN COMPOUNDS 400500 -- Photochemistry ; OXYGEN ; PHOTOCHEMICAL REACTIONS ; PHOTOCHEMISTRY ; Physical chemistry of induced reactions (with radiations, particles and ultrasonics) ; PROPANE ; RADICALS ; REACTION INTERMEDIATES ; SOLVENT PROPERTIES</subject><ispartof>J. Am. Chem. Soc.; (United States), 1987-04, Vol.109 (9), p.2780-2788</ispartof><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,883,27907,27908</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7482995$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/6800210$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>MIYASHI, T</creatorcontrib><creatorcontrib>KAMATA, M</creatorcontrib><creatorcontrib>MUKAI, T</creatorcontrib><creatorcontrib>Tohoku Univ., Sendai, Japan</creatorcontrib><title>Simultaneous capture of two distinct radical ion intermediates generated from the EDA complexes of three-membered compounds with TCNE by photoexcitation and in the dark</title><title>J. Am. Chem. Soc.; (United States)</title><description>Irradiation of the electron donor-acceptor (EDA) complexes of 2,2-diaryl-1-methylenecyclopropanes, 1,1,2,2-tetraarylcyclopropanes, 2,3-diaryloxiranes, or 2,3-diarylaziridines with tetracyanoethylene (TCNE) under aerated conditions involved oxygenation and/or the (3 + 2) cycloaddition with TCNE. The same oxygenation took place in the dark when the EDA complexes of 2,2-diaryl-1-methylenecyclopropanes or 1,1,2,2-tetraarylcyclopropanes with TCNE were simply stirred in oxygen-saturated solvents. Oxygenation occurred much more efficiently as the solvent polarity and the electron-donative nature of donor substrates increased. 1,2,4,5-Tetramethoxybenzene (TMB) used as a quencher efficiently suppressed oxygenation but not the (3 + 2) cycloaddition at all. Oxygenation occurs through the solvent-separated radical cations diffused from the photogenerated geminate radical ion pairs, whereas the cage coupling of the radical ion pairs involves the (3 + 2) cycloaddition with TCNE.</description><subject>ALKANES</subject><subject>ALKENES</subject><subject>CATIONS</subject><subject>CHARGED PARTICLES</subject><subject>CHEMICAL REACTIONS</subject><subject>CHEMISTRY</subject><subject>CYCLOALKANES</subject><subject>DATA</subject><subject>DIFFUSION</subject><subject>ELECTRON TRANSFER</subject><subject>ELEMENTS</subject><subject>EPOXIDES</subject><subject>Exact sciences and technology</subject><subject>EXPERIMENTAL DATA</subject><subject>General and physical chemistry</subject><subject>HYDROCARBONS</subject><subject>INFORMATION</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>IONS</subject><subject>NONMETALS</subject><subject>NUMERICAL DATA</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>ORGANIC OXYGEN COMPOUNDS 400500 -- Photochemistry</subject><subject>OXYGEN</subject><subject>PHOTOCHEMICAL REACTIONS</subject><subject>PHOTOCHEMISTRY</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>PROPANE</subject><subject>RADICALS</subject><subject>REACTION INTERMEDIATES</subject><subject>SOLVENT PROPERTIES</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNotUElOAzEQtBBIhMCJD1iI64CXWY9RCIsUwYFwHjl2m3HI2CPbI5If8UwcwqmXKlV1F0LXlNxRwuj9RhDCci4IL07QhBaMZAVl5SmakARkVV3yc3QRwiaNOavpBP28m37cRmHBjQFLMcTRA3Yax2-HlQnRWBmxF8pIscXGWWxsBN-DMiJCwJ9gwadOYe1dj2MHePEww9L1wxZ2iXCQ6jxA1kO_Bp-IB8yNVgX8bWKHV_PXBV7v8dC56GAnTRTx4COsSl5_ikr4r0t0psU2wNV_naKPx8Vq_pwt355e5rNl5ijLY8Y5LYmGWtKcpShUzivQdQNMVoWmkpZFWtaNJqTi0DR5o6kqGl1woRirgfIpujnquvR7G9I5IDvprAUZ27JOMVKSSLdH0iBCykV7YaUJ7eBNL_y-rfKaNU3BfwGfcXzm</recordid><startdate>19870429</startdate><enddate>19870429</enddate><creator>MIYASHI, T</creator><creator>KAMATA, M</creator><creator>MUKAI, T</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>OTOTI</scope></search><sort><creationdate>19870429</creationdate><title>Simultaneous capture of two distinct radical ion intermediates generated from the EDA complexes of three-membered compounds with TCNE by photoexcitation and in the dark</title><author>MIYASHI, T ; KAMATA, M ; MUKAI, T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-o124t-33160fe8c142024d437ef89e2c75f1c16524d89f0073e9949f1d59f53ad228e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>ALKANES</topic><topic>ALKENES</topic><topic>CATIONS</topic><topic>CHARGED PARTICLES</topic><topic>CHEMICAL REACTIONS</topic><topic>CHEMISTRY</topic><topic>CYCLOALKANES</topic><topic>DATA</topic><topic>DIFFUSION</topic><topic>ELECTRON TRANSFER</topic><topic>ELEMENTS</topic><topic>EPOXIDES</topic><topic>Exact sciences and technology</topic><topic>EXPERIMENTAL DATA</topic><topic>General and physical chemistry</topic><topic>HYDROCARBONS</topic><topic>INFORMATION</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>IONS</topic><topic>NONMETALS</topic><topic>NUMERICAL DATA</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>ORGANIC OXYGEN COMPOUNDS 400500 -- Photochemistry</topic><topic>OXYGEN</topic><topic>PHOTOCHEMICAL REACTIONS</topic><topic>PHOTOCHEMISTRY</topic><topic>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</topic><topic>PROPANE</topic><topic>RADICALS</topic><topic>REACTION INTERMEDIATES</topic><topic>SOLVENT PROPERTIES</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MIYASHI, T</creatorcontrib><creatorcontrib>KAMATA, M</creatorcontrib><creatorcontrib>MUKAI, T</creatorcontrib><creatorcontrib>Tohoku Univ., Sendai, Japan</creatorcontrib><collection>Pascal-Francis</collection><collection>OSTI.GOV</collection><jtitle>J. Am. Chem. Soc.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>MIYASHI, T</au><au>KAMATA, M</au><au>MUKAI, T</au><aucorp>Tohoku Univ., Sendai, Japan</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Simultaneous capture of two distinct radical ion intermediates generated from the EDA complexes of three-membered compounds with TCNE by photoexcitation and in the dark</atitle><jtitle>J. Am. Chem. Soc.; (United States)</jtitle><date>1987-04-29</date><risdate>1987</risdate><volume>109</volume><issue>9</issue><spage>2780</spage><epage>2788</epage><pages>2780-2788</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Irradiation of the electron donor-acceptor (EDA) complexes of 2,2-diaryl-1-methylenecyclopropanes, 1,1,2,2-tetraarylcyclopropanes, 2,3-diaryloxiranes, or 2,3-diarylaziridines with tetracyanoethylene (TCNE) under aerated conditions involved oxygenation and/or the (3 + 2) cycloaddition with TCNE. The same oxygenation took place in the dark when the EDA complexes of 2,2-diaryl-1-methylenecyclopropanes or 1,1,2,2-tetraarylcyclopropanes with TCNE were simply stirred in oxygen-saturated solvents. Oxygenation occurred much more efficiently as the solvent polarity and the electron-donative nature of donor substrates increased. 1,2,4,5-Tetramethoxybenzene (TMB) used as a quencher efficiently suppressed oxygenation but not the (3 + 2) cycloaddition at all. Oxygenation occurs through the solvent-separated radical cations diffused from the photogenerated geminate radical ion pairs, whereas the cage coupling of the radical ion pairs involves the (3 + 2) cycloaddition with TCNE.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ja00243a035</doi><tpages>9</tpages></addata></record> |
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| ispartof | J. Am. Chem. Soc.; (United States), 1987-04, Vol.109 (9), p.2780-2788 |
| issn | 0002-7863 1520-5126 |
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| subjects | ALKANES ALKENES CATIONS CHARGED PARTICLES CHEMICAL REACTIONS CHEMISTRY CYCLOALKANES DATA DIFFUSION ELECTRON TRANSFER ELEMENTS EPOXIDES Exact sciences and technology EXPERIMENTAL DATA General and physical chemistry HYDROCARBONS INFORMATION INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY IONS NONMETALS NUMERICAL DATA ORGANIC COMPOUNDS ORGANIC NITROGEN COMPOUNDS ORGANIC OXYGEN COMPOUNDS 400500 -- Photochemistry OXYGEN PHOTOCHEMICAL REACTIONS PHOTOCHEMISTRY Physical chemistry of induced reactions (with radiations, particles and ultrasonics) PROPANE RADICALS REACTION INTERMEDIATES SOLVENT PROPERTIES |
| title | Simultaneous capture of two distinct radical ion intermediates generated from the EDA complexes of three-membered compounds with TCNE by photoexcitation and in the dark |
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