Template-Assisted Stereoselective Photocyclodimerization of 2-Anthracenecarboxylic Acid by Bispyridinio-Appended γ-Cyclodextrin
Four kinds of bispyridinio-appended γ-cyclodextrin (γ-CD) were prepared to make a molecular flask for controlling the stereoselectivity of photocyclodimerization of 2-anthracenecarboxylate. When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio...
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| Veröffentlicht in: | Journal of organic chemistry 2005-02, Vol.70 (4), p.1237-1242 |
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| container_title | Journal of organic chemistry |
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| creator | Ikeda, Hiroshi Nihei, Takashi Ueno, Akihiko |
| description | Four kinds of bispyridinio-appended γ-cyclodextrin (γ-CD) were prepared to make a molecular flask for controlling the stereoselectivity of photocyclodimerization of 2-anthracenecarboxylate. When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio-appended γ-CD, the relative yield of one of the configurational isomers, the head-to-head/anti-isomer, was increased 1.8-fold compared to the corresponding yield in the presence of unmodified γ-CD or in the absence of any γ-CD. The optical yields of the photocyclodimerization reaction products also increased more than 10-fold by the addition of bispyridinio-appended γ-CD compared with unmodified γ-CD. |
| doi_str_mv | 10.1021/jo0482817 |
| format | Article |
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When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio-appended γ-CD, the relative yield of one of the configurational isomers, the head-to-head/anti-isomer, was increased 1.8-fold compared to the corresponding yield in the presence of unmodified γ-CD or in the absence of any γ-CD. The optical yields of the photocyclodimerization reaction products also increased more than 10-fold by the addition of bispyridinio-appended γ-CD compared with unmodified γ-CD.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0482817</identifier><identifier>PMID: 15704956</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anthracenes - chemistry ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Carboxylic Acids - chemistry ; Chemistry ; Condensed benzenic and aromatic compounds ; Dimerization ; Exact sciences and technology ; gamma-Cyclodextrins - chemistry ; General and physical chemistry ; Molecular Structure ; Organic chemistry ; Photochemistry ; Physical chemistry of induced reactions (with radiations, particles and ultrasonics) ; Preparations and properties ; Pyridines - chemistry</subject><ispartof>Journal of organic chemistry, 2005-02, Vol.70 (4), p.1237-1242</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-a3e089960d60f8ef763cff1f7d5ca80de030db0c361032b43548f0ab6b08b33d3</citedby><cites>FETCH-LOGICAL-a381t-a3e089960d60f8ef763cff1f7d5ca80de030db0c361032b43548f0ab6b08b33d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0482817$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0482817$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16538552$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15704956$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ikeda, Hiroshi</creatorcontrib><creatorcontrib>Nihei, Takashi</creatorcontrib><creatorcontrib>Ueno, Akihiko</creatorcontrib><title>Template-Assisted Stereoselective Photocyclodimerization of 2-Anthracenecarboxylic Acid by Bispyridinio-Appended γ-Cyclodextrin</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Four kinds of bispyridinio-appended γ-cyclodextrin (γ-CD) were prepared to make a molecular flask for controlling the stereoselectivity of photocyclodimerization of 2-anthracenecarboxylate. When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio-appended γ-CD, the relative yield of one of the configurational isomers, the head-to-head/anti-isomer, was increased 1.8-fold compared to the corresponding yield in the presence of unmodified γ-CD or in the absence of any γ-CD. The optical yields of the photocyclodimerization reaction products also increased more than 10-fold by the addition of bispyridinio-appended γ-CD compared with unmodified γ-CD.</description><subject>Anthracenes - chemistry</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Carboxylic Acids - chemistry</subject><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Dimerization</subject><subject>Exact sciences and technology</subject><subject>gamma-Cyclodextrins - chemistry</subject><subject>General and physical chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Photochemistry</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>Preparations and properties</subject><subject>Pyridines - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcFu1DAQhi0EokvhwAugXEDiEBjbsZMcwwpapEoUdRFSL5FjT1SXJA62F2048U68B8-Ey666F3yYOcynT79-E_KcwhsKjL69dVBUrKLlA7KigkEuaygekhUAYzlnkp-QJyHcQnpCiMfkhIoSilrIFfm1wXEeVMS8CcGGiCa7iujRBRxQR_sDs8sbF51e9OCMHdHbnypaN2Wuz1jeTPHGK40TauU7t1sGq7NGW5N1S_bOhnnx1tjJuryZZ5xM0v_5na__yXAXvZ2ekke9GgI-O-xT8uXD-836PL_4dPZx3Vzkilc0polQ1bUEI6GvsC8l131P-9IIrSowCBxMB5pLCpx1BRdF1YPqZAdVx7nhp-TV3jt7932LIbajDRqHQU3otqGVZcF4CXUCX-9B7V0IHvt29nZUfmkptHd1t_d1J_bFQbrtRjRH8tBvAl4eABW0GnqvJm3DkZOCV0KwxOV77u4Ldvd35b-lYLwU7ebyqj0X9Prz9Zlovx69SoeUZ-un1N1_Av4FsQSl2A</recordid><startdate>20050218</startdate><enddate>20050218</enddate><creator>Ikeda, Hiroshi</creator><creator>Nihei, Takashi</creator><creator>Ueno, Akihiko</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050218</creationdate><title>Template-Assisted Stereoselective Photocyclodimerization of 2-Anthracenecarboxylic Acid by Bispyridinio-Appended γ-Cyclodextrin</title><author>Ikeda, Hiroshi ; Nihei, Takashi ; Ueno, Akihiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-a3e089960d60f8ef763cff1f7d5ca80de030db0c361032b43548f0ab6b08b33d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Anthracenes - chemistry</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Carboxylic Acids - chemistry</topic><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Dimerization</topic><topic>Exact sciences and technology</topic><topic>gamma-Cyclodextrins - chemistry</topic><topic>General and physical chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Photochemistry</topic><topic>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</topic><topic>Preparations and properties</topic><topic>Pyridines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ikeda, Hiroshi</creatorcontrib><creatorcontrib>Nihei, Takashi</creatorcontrib><creatorcontrib>Ueno, Akihiko</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>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ikeda, Hiroshi</au><au>Nihei, Takashi</au><au>Ueno, Akihiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Template-Assisted Stereoselective Photocyclodimerization of 2-Anthracenecarboxylic Acid by Bispyridinio-Appended γ-Cyclodextrin</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-02-18</date><risdate>2005</risdate><volume>70</volume><issue>4</issue><spage>1237</spage><epage>1242</epage><pages>1237-1242</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Four kinds of bispyridinio-appended γ-cyclodextrin (γ-CD) were prepared to make a molecular flask for controlling the stereoselectivity of photocyclodimerization of 2-anthracenecarboxylate. When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio-appended γ-CD, the relative yield of one of the configurational isomers, the head-to-head/anti-isomer, was increased 1.8-fold compared to the corresponding yield in the presence of unmodified γ-CD or in the absence of any γ-CD. The optical yields of the photocyclodimerization reaction products also increased more than 10-fold by the addition of bispyridinio-appended γ-CD compared with unmodified γ-CD.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15704956</pmid><doi>10.1021/jo0482817</doi><tpages>6</tpages></addata></record> |
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| language | eng |
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| subjects | Anthracenes - chemistry Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Carboxylic Acids - chemistry Chemistry Condensed benzenic and aromatic compounds Dimerization Exact sciences and technology gamma-Cyclodextrins - chemistry General and physical chemistry Molecular Structure Organic chemistry Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Preparations and properties Pyridines - chemistry |
| title | Template-Assisted Stereoselective Photocyclodimerization of 2-Anthracenecarboxylic Acid by Bispyridinio-Appended γ-Cyclodextrin |
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