Synthesis of Trifluoromethyl-Substituted Arenes, Cyclohexenones and Pyran-4-ones by Cyclocondensation of 1,3-Bis(silyloxy)-1,3-butadienes with 4,4-Dimethoxy-1,1,1-trifluorobut-3-en-2-one: Influence of the Lewis Acid on the Product Distribution
The TiCl4-mediated formal [3 + 3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one afforded a variety of functionalized 4-methoxy-6-(trifluoromethyl)salicylates and 3-methoxy-5-(trifluoromethyl)phenols with very good regioselectivity. Th...
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| Veröffentlicht in: | Journal of organic chemistry 2009-07, Vol.74 (14), p.5002-5010 |
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| creator | Bunescu, Alina Reimann, Sebastian Lubbe, Mathias Spannenberg, Anke Langer, Peter |
| description | The TiCl4-mediated formal [3 + 3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one afforded a variety of functionalized 4-methoxy-6-(trifluoromethyl)salicylates and 3-methoxy-5-(trifluoromethyl)phenols with very good regioselectivity. The Me3SiOTf-mediated cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, containing no substituent located at carbon atom C-4 of the diene (R1 = H), resulted in the formation of trifluoromethyl-substituted pyran-4-ones. In contrast, trifluoromethylated cyclohexenones were formed when dienes were employed which do contain a substituent located at carbon C-4 (R1 ≠ H). |
| doi_str_mv | 10.1021/jo900702u |
| format | Article |
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The Me3SiOTf-mediated cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, containing no substituent located at carbon atom C-4 of the diene (R1 = H), resulted in the formation of trifluoromethyl-substituted pyran-4-ones. In contrast, trifluoromethylated cyclohexenones were formed when dienes were employed which do contain a substituent located at carbon C-4 (R1 ≠ H).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo900702u</identifier><identifier>PMID: 19480453</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Chemistry, Pharmaceutical ; Cyclization ; Exact sciences and technology ; Fluorine - chemistry ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Hydrocarbons, Fluorinated - chemistry ; Ligands ; Methane - chemistry ; Molecular Structure ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Pyrans - chemistry</subject><ispartof>Journal of organic chemistry, 2009-07, Vol.74 (14), p.5002-5010</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-3e058c419a99bd0ecee0d4e26b63501d3672b3a19479898dc8daa326045c61733</citedby><cites>FETCH-LOGICAL-a343t-3e058c419a99bd0ecee0d4e26b63501d3672b3a19479898dc8daa326045c61733</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/jo900702u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo900702u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22087205$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19480453$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bunescu, Alina</creatorcontrib><creatorcontrib>Reimann, Sebastian</creatorcontrib><creatorcontrib>Lubbe, Mathias</creatorcontrib><creatorcontrib>Spannenberg, Anke</creatorcontrib><creatorcontrib>Langer, Peter</creatorcontrib><title>Synthesis of Trifluoromethyl-Substituted Arenes, Cyclohexenones and Pyran-4-ones by Cyclocondensation of 1,3-Bis(silyloxy)-1,3-butadienes with 4,4-Dimethoxy-1,1,1-trifluorobut-3-en-2-one: Influence of the Lewis Acid on the Product Distribution</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The TiCl4-mediated formal [3 + 3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one afforded a variety of functionalized 4-methoxy-6-(trifluoromethyl)salicylates and 3-methoxy-5-(trifluoromethyl)phenols with very good regioselectivity. The Me3SiOTf-mediated cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, containing no substituent located at carbon atom C-4 of the diene (R1 = H), resulted in the formation of trifluoromethyl-substituted pyran-4-ones. In contrast, trifluoromethylated cyclohexenones were formed when dienes were employed which do contain a substituent located at carbon C-4 (R1 ≠ H).</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Chemistry, Pharmaceutical</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Fluorine - chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Hydrocarbons, Fluorinated - chemistry</subject><subject>Ligands</subject><subject>Methane - chemistry</subject><subject>Molecular Structure</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrans - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkd1uEzEQhS0EoiFwwQsg34CoFIPX3l_uQspPpUhUarleee1ZxdXGLrZX7T53X6CzJLQ32BeWR5_OmZlDyNuMf8q4yD5f-4bziovxGVlkheCsbHj-nCw4F4JJUcoT8irGa46nKIqX5CRr8prnhVyQ-8vJpR1EG6nv6VWw_TD64PeQdtPALscuJpvGBIauAziIK7qZ9OB3cAfO458qZ-jFFJRjOftb6KYDor0z4KJK1rtZO1tJ9tXGj9EO0-DvplM2V7oxKWNnZXpr047mq5yd2dkeESTwsvSvK4SZZOCYmK2-0HOHdXAaZn2cgm7hFgdZa2soms6Vi-DNqBM9sxFlUAC7eU1e9GqI8Ob4Lsnv79-uNj_Z9teP8816y5TMJToBL2qdZ41qms5w0ADc5CDKrpQFz4wsK9FJhbusmrqpja6NUrhtXKwus0rKJflw0L0J_s8IMbV7GzUMg3Lgx9iWVV7xBuNZktMDqIOPMUDf3gS7V2FqM97OCbePCSP77ig6dnswT-QxUgTeHwEVtRp6jEbb-MgJwetK8OKJUzqi_hgc7uI_hg_82rxL</recordid><startdate>20090717</startdate><enddate>20090717</enddate><creator>Bunescu, Alina</creator><creator>Reimann, Sebastian</creator><creator>Lubbe, Mathias</creator><creator>Spannenberg, Anke</creator><creator>Langer, Peter</creator><general>American Chemical Society</general><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>20090717</creationdate><title>Synthesis of Trifluoromethyl-Substituted Arenes, Cyclohexenones and Pyran-4-ones by Cyclocondensation of 1,3-Bis(silyloxy)-1,3-butadienes with 4,4-Dimethoxy-1,1,1-trifluorobut-3-en-2-one: Influence of the Lewis Acid on the Product Distribution</title><author>Bunescu, Alina ; Reimann, Sebastian ; Lubbe, Mathias ; Spannenberg, Anke ; Langer, Peter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-3e058c419a99bd0ecee0d4e26b63501d3672b3a19479898dc8daa326045c61733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Chemistry, Pharmaceutical</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Fluorine - chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Hydrocarbons, Fluorinated - chemistry</topic><topic>Ligands</topic><topic>Methane - chemistry</topic><topic>Molecular Structure</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyrans - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bunescu, Alina</creatorcontrib><creatorcontrib>Reimann, Sebastian</creatorcontrib><creatorcontrib>Lubbe, Mathias</creatorcontrib><creatorcontrib>Spannenberg, Anke</creatorcontrib><creatorcontrib>Langer, Peter</creatorcontrib><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>Bunescu, Alina</au><au>Reimann, Sebastian</au><au>Lubbe, Mathias</au><au>Spannenberg, Anke</au><au>Langer, Peter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Trifluoromethyl-Substituted Arenes, Cyclohexenones and Pyran-4-ones by Cyclocondensation of 1,3-Bis(silyloxy)-1,3-butadienes with 4,4-Dimethoxy-1,1,1-trifluorobut-3-en-2-one: Influence of the Lewis Acid on the Product Distribution</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-07-17</date><risdate>2009</risdate><volume>74</volume><issue>14</issue><spage>5002</spage><epage>5010</epage><pages>5002-5010</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The TiCl4-mediated formal [3 + 3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one afforded a variety of functionalized 4-methoxy-6-(trifluoromethyl)salicylates and 3-methoxy-5-(trifluoromethyl)phenols with very good regioselectivity. The Me3SiOTf-mediated cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, containing no substituent located at carbon atom C-4 of the diene (R1 = H), resulted in the formation of trifluoromethyl-substituted pyran-4-ones. In contrast, trifluoromethylated cyclohexenones were formed when dienes were employed which do contain a substituent located at carbon C-4 (R1 ≠ H).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19480453</pmid><doi>10.1021/jo900702u</doi><tpages>9</tpages></addata></record> |
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| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Chemistry, Pharmaceutical Cyclization Exact sciences and technology Fluorine - chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Hydrocarbons, Fluorinated - chemistry Ligands Methane - chemistry Molecular Structure Noncondensed benzenic compounds Organic chemistry Preparations and properties Pyrans - chemistry |
| title | Synthesis of Trifluoromethyl-Substituted Arenes, Cyclohexenones and Pyran-4-ones by Cyclocondensation of 1,3-Bis(silyloxy)-1,3-butadienes with 4,4-Dimethoxy-1,1,1-trifluorobut-3-en-2-one: Influence of the Lewis Acid on the Product Distribution |
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