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Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group
An efficient, microwave‐assisted and ionic‐liquid‐catalyzed esterification of bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters is presented. The latter were subjected to a base‐catalyzed isomerization reaction, which proceeded with the r...
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| Published in: | European Journal of Organic Chemistry 2011-06, Vol.2011 (18), p.3368-3374 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3574-7602f21aa9f1d2d1141fda8f0c3395b89f6e70aa9a9e0ffbf53748c2089e85753 |
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| cites | cdi_FETCH-LOGICAL-c3574-7602f21aa9f1d2d1141fda8f0c3395b89f6e70aa9a9e0ffbf53748c2089e85753 |
| container_end_page | 3374 |
| container_issue | 18 |
| container_start_page | 3368 |
| container_title | European Journal of Organic Chemistry |
| container_volume | 2011 |
| creator | Hren, Jure Perdih, Franc Polanc, Slovenko Kočevar, Marijan |
| description | An efficient, microwave‐assisted and ionic‐liquid‐catalyzed esterification of bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters is presented. The latter were subjected to a base‐catalyzed isomerization reaction, which proceeded with the retention of symmetry.
Bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid tetraesters have been prepared in a green ionic‐liquid‐catalyzed microwave‐assisted reaction from the correspondingdianhydrides. The tetraesters isomerize in a base‐catalyzed isomerization reaction to give symmetrical products in high yields. |
| doi_str_mv | 10.1002/ejoc.201100104 |
| format | article |
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Bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid tetraesters have been prepared in a green ionic‐liquid‐catalyzed microwave‐assisted reaction from the correspondingdianhydrides. The tetraesters isomerize in a base‐catalyzed isomerization reaction to give symmetrical products in high yields.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201100104</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Bicyclic compounds ; Chemistry ; Exact sciences and technology ; Green chemistry ; Ionic liquids ; Isomerization ; Microwave chemistry ; Organic chemistry ; Preparations and properties</subject><ispartof>European Journal of Organic Chemistry, 2011-06, Vol.2011 (18), p.3368-3374</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3574-7602f21aa9f1d2d1141fda8f0c3395b89f6e70aa9a9e0ffbf53748c2089e85753</citedby><cites>FETCH-LOGICAL-c3574-7602f21aa9f1d2d1141fda8f0c3395b89f6e70aa9a9e0ffbf53748c2089e85753</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>313,314,776,780,788,27899,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24253292$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Hren, Jure</creatorcontrib><creatorcontrib>Perdih, Franc</creatorcontrib><creatorcontrib>Polanc, Slovenko</creatorcontrib><creatorcontrib>Kočevar, Marijan</creatorcontrib><title>Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>An efficient, microwave‐assisted and ionic‐liquid‐catalyzed esterification of bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters is presented. The latter were subjected to a base‐catalyzed isomerization reaction, which proceeded with the retention of symmetry.
Bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid tetraesters have been prepared in a green ionic‐liquid‐catalyzed microwave‐assisted reaction from the correspondingdianhydrides. The tetraesters isomerize in a base‐catalyzed isomerization reaction to give symmetrical products in high yields.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Bicyclic compounds</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Green chemistry</subject><subject>Ionic liquids</subject><subject>Isomerization</subject><subject>Microwave chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkMtLAzEQxhdRsD6unnPxuHWS7CtHW21VihVfFURCzE5sartbki26_vVuXSneJIfJzHy_b-ALgiMKXQrATnBW6i4D2jQUoq2gQ0GIEBIB280_4lFIBX_aDfa8nwGASBLaCfwtVlhUtixIachdvVhg5WryiM6vPDlD307sl_rRmNKRntW1npfPrNu8l1I3PHpiC1JNkdw49FhoXLsp0nM2f8MpqpycLmyOZOjK1fIg2DFq7vHwt-4HD4Pz-_5FOBoPL_uno1DzOI3CNAFmGFVKGJqznNKImlxlBjTnIn7NhEkwhWatBIIxrybmaZRpBpnALE5jvh90W1_tSu8dGrl0dqFcLSnIdWRyHZncRNYAxy2wVF6ruXGq0NZvKBaxmDPBGp1odR92jvU_rvL8atz_eyNsWesr_Nywyr3LJOVpLCfXQ9mfJJOLwUjIhH8DRF6NAg</recordid><startdate>201106</startdate><enddate>201106</enddate><creator>Hren, Jure</creator><creator>Perdih, Franc</creator><creator>Polanc, Slovenko</creator><creator>Kočevar, Marijan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201106</creationdate><title>Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group</title><author>Hren, Jure ; Perdih, Franc ; Polanc, Slovenko ; Kočevar, Marijan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3574-7602f21aa9f1d2d1141fda8f0c3395b89f6e70aa9a9e0ffbf53748c2089e85753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Bicyclic compounds</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Green chemistry</topic><topic>Ionic liquids</topic><topic>Isomerization</topic><topic>Microwave chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hren, Jure</creatorcontrib><creatorcontrib>Perdih, Franc</creatorcontrib><creatorcontrib>Polanc, Slovenko</creatorcontrib><creatorcontrib>Kočevar, Marijan</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hren, Jure</au><au>Perdih, Franc</au><au>Polanc, Slovenko</au><au>Kočevar, Marijan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2011-06</date><risdate>2011</risdate><volume>2011</volume><issue>18</issue><spage>3368</spage><epage>3374</epage><pages>3368-3374</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient, microwave‐assisted and ionic‐liquid‐catalyzed esterification of bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters is presented. The latter were subjected to a base‐catalyzed isomerization reaction, which proceeded with the retention of symmetry.
Bicyclo[2.2.2]oct‐7‐ene‐2,3,5,6‐tetracarboxylic acid tetraesters have been prepared in a green ionic‐liquid‐catalyzed microwave‐assisted reaction from the correspondingdianhydrides. The tetraesters isomerize in a base‐catalyzed isomerization reaction to give symmetrical products in high yields.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201100104</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 1434-193X |
| ispartof | European Journal of Organic Chemistry, 2011-06, Vol.2011 (18), p.3368-3374 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_201100104 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Bicyclic compounds Chemistry Exact sciences and technology Green chemistry Ionic liquids Isomerization Microwave chemistry Organic chemistry Preparations and properties |
| title | Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group |
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