Light-induced Dehydrodimerization of 3-Hydroxypyrroles
Irradiation (λ > 280 nm) of 3‐hydroxy‐1H‐pyrrole‐2‐carboxylates 1 in CH3CN gives the [2.2′‐bi(3‐oxo‐2,3‐dihydro‐1H‐pyrrole)]‐2‐,2′‐dicarboxylates 2 in reasonable to good yields. The corresponding N‐methylpyrroles 3 only undergo slow photodecomposition under similar conditions. Several 2‐methyl‐3‐...
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| Veröffentlicht in: | Helvetica chimica acta 1984-11, Vol.67 (7), p.1957-1962 |
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| container_end_page | 1962 |
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| container_issue | 7 |
| container_start_page | 1957 |
| container_title | Helvetica chimica acta |
| container_volume | 67 |
| creator | Ghaffari-Tabrizi, Ramin Margaretha, Paul Schmalle, Helmut W. |
| description | Irradiation (λ > 280 nm) of 3‐hydroxy‐1H‐pyrrole‐2‐carboxylates 1 in CH3CN gives the [2.2′‐bi(3‐oxo‐2,3‐dihydro‐1H‐pyrrole)]‐2‐,2′‐dicarboxylates 2 in reasonable to good yields. The corresponding N‐methylpyrroles 3 only undergo slow photodecomposition under similar conditions. Several 2‐methyl‐3‐oxo‐2,3‐dihydro‐1H‐pyrrole‐2‐carboxylates 4 and 5 were synthesized to compare their spectral data with those of the dehydrodimers 2. A X‐ray structure analysis was performed for diethyl [2,2′‐bi(4,5‐dimethyl‐3‐oxo‐2,3‐dihydro‐1 H‐pyrrole)]‐2,2′‐dicarboxylate (2b). The originally proposed [3,3′‐bi(3H‐pyroole)] structure for compounds 2a‐e proves incorrect. |
| doi_str_mv | 10.1002/hlca.19840670734 |
| format | Article |
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The corresponding N‐methylpyrroles 3 only undergo slow photodecomposition under similar conditions. Several 2‐methyl‐3‐oxo‐2,3‐dihydro‐1H‐pyrrole‐2‐carboxylates 4 and 5 were synthesized to compare their spectral data with those of the dehydrodimers 2. A X‐ray structure analysis was performed for diethyl [2,2′‐bi(4,5‐dimethyl‐3‐oxo‐2,3‐dihydro‐1 H‐pyrrole)]‐2,2′‐dicarboxylate (2b). The originally proposed [3,3′‐bi(3H‐pyroole)] structure for compounds 2a‐e proves incorrect.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.19840670734</identifier><identifier>CODEN: HCACAV</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><subject>Chemistry ; Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Organic chemistry ; Organic compounds ; Physics ; Preparations and properties ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Helvetica chimica acta, 1984-11, Vol.67 (7), p.1957-1962</ispartof><rights>Copyright © 1984 Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1985 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3624-10501a9a4a8fc695e91b88d22f9fb73457aff008dbbb37e199c6f91e76c4c97c3</citedby><cites>FETCH-LOGICAL-c3624-10501a9a4a8fc695e91b88d22f9fb73457aff008dbbb37e199c6f91e76c4c97c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fhlca.19840670734$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.19840670734$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8865874$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Ghaffari-Tabrizi, Ramin</creatorcontrib><creatorcontrib>Margaretha, Paul</creatorcontrib><creatorcontrib>Schmalle, Helmut W.</creatorcontrib><title>Light-induced Dehydrodimerization of 3-Hydroxypyrroles</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>Irradiation (λ > 280 nm) of 3‐hydroxy‐1H‐pyrrole‐2‐carboxylates 1 in CH3CN gives the [2.2′‐bi(3‐oxo‐2,3‐dihydro‐1H‐pyrrole)]‐2‐,2′‐dicarboxylates 2 in reasonable to good yields. The corresponding N‐methylpyrroles 3 only undergo slow photodecomposition under similar conditions. Several 2‐methyl‐3‐oxo‐2,3‐dihydro‐1H‐pyrrole‐2‐carboxylates 4 and 5 were synthesized to compare their spectral data with those of the dehydrodimers 2. A X‐ray structure analysis was performed for diethyl [2,2′‐bi(4,5‐dimethyl‐3‐oxo‐2,3‐dihydro‐1 H‐pyrrole)]‐2,2′‐dicarboxylate (2b). The originally proposed [3,3′‐bi(3H‐pyroole)] structure for compounds 2a‐e proves incorrect.</description><subject>Chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Preparations and properties</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><recordid>eNqFjz1PwzAQhi0EEqWwM3ZgdTnHiT8GhqqFFhHBAmo3y3Fsakibyi6i4dfTKKiCiemk0_u8dw9ClwSGBCC5XlZGD4kUKTAOnKZHqEeyJMEJ49kx6gEQgYHIxSk6i_ENAKQE3kMs96_LLfbr8sPYcjCxy6YMdelXNvgvvfX1elC7AcWzdr1rNk0IdWXjOTpxuor24mf20cvd7fN4hvOn6f14lGNDWZJiAhkQLXWqhTNMZlaSQogySZx0xf7JjGvnAERZFAXllkhpmJPEcmZSI7mhfQRdrwl1jME6tQl-pUOjCKjWW7Xe6pf3HrnqkI2ORlcu6LXx8cAJwTLB29hNF_v0lW3-rVWzfDz6ewZ3vI9buzvwOrwrxinP1Pxxqh7IdALzh4Va0G8W23nx</recordid><startdate>19841107</startdate><enddate>19841107</enddate><creator>Ghaffari-Tabrizi, Ramin</creator><creator>Margaretha, Paul</creator><creator>Schmalle, Helmut W.</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19841107</creationdate><title>Light-induced Dehydrodimerization of 3-Hydroxypyrroles</title><author>Ghaffari-Tabrizi, Ramin ; Margaretha, Paul ; Schmalle, Helmut W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3624-10501a9a4a8fc695e91b88d22f9fb73457aff008dbbb37e199c6f91e76c4c97c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Preparations and properties</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ghaffari-Tabrizi, Ramin</creatorcontrib><creatorcontrib>Margaretha, Paul</creatorcontrib><creatorcontrib>Schmalle, Helmut W.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ghaffari-Tabrizi, Ramin</au><au>Margaretha, Paul</au><au>Schmalle, Helmut W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Light-induced Dehydrodimerization of 3-Hydroxypyrroles</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>1984-11-07</date><risdate>1984</risdate><volume>67</volume><issue>7</issue><spage>1957</spage><epage>1962</epage><pages>1957-1962</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><coden>HCACAV</coden><abstract>Irradiation (λ > 280 nm) of 3‐hydroxy‐1H‐pyrrole‐2‐carboxylates 1 in CH3CN gives the [2.2′‐bi(3‐oxo‐2,3‐dihydro‐1H‐pyrrole)]‐2‐,2′‐dicarboxylates 2 in reasonable to good yields. The corresponding N‐methylpyrroles 3 only undergo slow photodecomposition under similar conditions. Several 2‐methyl‐3‐oxo‐2,3‐dihydro‐1H‐pyrrole‐2‐carboxylates 4 and 5 were synthesized to compare their spectral data with those of the dehydrodimers 2. A X‐ray structure analysis was performed for diethyl [2,2′‐bi(4,5‐dimethyl‐3‐oxo‐2,3‐dihydro‐1 H‐pyrrole)]‐2,2′‐dicarboxylate (2b). The originally proposed [3,3′‐bi(3H‐pyroole)] structure for compounds 2a‐e proves incorrect.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/hlca.19840670734</doi><tpages>6</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Organic compounds Physics Preparations and properties Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | Light-induced Dehydrodimerization of 3-Hydroxypyrroles |
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