Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β‑Elimination of Sulfonyl Radicals to Form Polycyclic Imines
Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cy...
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| Veröffentlicht in: | Journal of the American Chemical Society 2013-11, Vol.135 (44), p.16610-16617 |
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| container_title | Journal of the American Chemical Society |
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| creator | Zhang, Hanmo Hay, E. Ben Geib, Steven J Curran, Dennis P |
| description | Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3,4-dihydroquinolines can also be produced by radical translocation reactions of N-(2-iodophenylsulfonyl)tetrahydroiso-quinolines. In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions. |
| doi_str_mv | 10.1021/ja408387d |
| format | Article |
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In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions.</description><identifier>ISSN: 0002-7863</identifier><identifier>ISSN: 1520-5126</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja408387d</identifier><identifier>PMID: 24111991</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>amines ; Crystallography, X-Ray ; Cyclization ; free radicals ; Free Radicals - chemistry ; Imines - chemical synthesis ; Imines - chemistry ; Models, Molecular ; Molecular Structure ; Polycyclic Compounds - chemical synthesis ; Polycyclic Compounds - chemistry ; sulfonamides ; Sulfonamides - chemical synthesis ; Sulfonamides - chemistry ; Sulfones - chemistry</subject><ispartof>Journal of the American Chemical Society, 2013-11, Vol.135 (44), p.16610-16617</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a438t-f45594c08d454d537b03ac2b1f26dbd4832692e9e6ab8e45f8d89df58b9a1ffa3</citedby><cites>FETCH-LOGICAL-a438t-f45594c08d454d537b03ac2b1f26dbd4832692e9e6ab8e45f8d89df58b9a1ffa3</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/ja408387d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja408387d$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2756,27067,27915,27916,56729,56779</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24111991$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Hanmo</creatorcontrib><creatorcontrib>Hay, E. Ben</creatorcontrib><creatorcontrib>Geib, Steven J</creatorcontrib><creatorcontrib>Curran, Dennis P</creatorcontrib><title>Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β‑Elimination of Sulfonyl Radicals to Form Polycyclic Imines</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3,4-dihydroquinolines can also be produced by radical translocation reactions of N-(2-iodophenylsulfonyl)tetrahydroiso-quinolines. In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions.</description><subject>amines</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>free radicals</subject><subject>Free Radicals - chemistry</subject><subject>Imines - chemical synthesis</subject><subject>Imines - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Polycyclic Compounds - chemical synthesis</subject><subject>Polycyclic Compounds - chemistry</subject><subject>sulfonamides</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfones - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU2KFDEYhoMoTju68AKSjaCL0vxXshGGpkcHBkb8WYdUfpw0qcqYVCk9K6_gVTyIh_Ak1lhtoyC4Ch953ofkewF4iNEzjAh-vjUMSSpbdwusMCeo4ZiI22CFECJNKwU9Avdq3c4jIxLfBUeEYYyVwitw_ca4aE2C651N8dqMMQ8V5rDMFm4GD99OKeTB9NH5Ci-snQr8HMdL-P3bjy9fNyn2cfiVu4kt7C7BvbfCMcPTXHr4OqedXaRnc8LX--BOmAH_YH8eg_enm3frV835xcuz9cl5YxiVYxMY54pZJB3jzHHadogaSzociHCdY5ISoYhXXphOesaDdFK5wGWnDA7B0GPwYvFeTV3vnfXDWEzSVyX2pux0NlH_fTPES_0hf9JUinl3chY82QtK_jj5Ouo-VutTMoPPU9WEUawER0j9F8VMKMEob9sZfbqgtuRaiw-HF2Gkb2rVh1pn9tGfXziQv3ucgccLYGzV2zyVYd7oP0Q_AfhrrTE</recordid><startdate>20131106</startdate><enddate>20131106</enddate><creator>Zhang, Hanmo</creator><creator>Hay, E. 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Ben</au><au>Geib, Steven J</au><au>Curran, Dennis P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β‑Elimination of Sulfonyl Radicals to Form Polycyclic Imines</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2013-11-06</date><risdate>2013</risdate><volume>135</volume><issue>44</issue><spage>16610</spage><epage>16617</epage><pages>16610-16617</pages><issn>0002-7863</issn><issn>1520-5126</issn><eissn>1520-5126</eissn><abstract>Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3,4-dihydroquinolines can also be produced by radical translocation reactions of N-(2-iodophenylsulfonyl)tetrahydroiso-quinolines. In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24111991</pmid><doi>10.1021/ja408387d</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of the American Chemical Society, 2013-11, Vol.135 (44), p.16610-16617 |
| issn | 0002-7863 1520-5126 1520-5126 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | amines Crystallography, X-Ray Cyclization free radicals Free Radicals - chemistry Imines - chemical synthesis Imines - chemistry Models, Molecular Molecular Structure Polycyclic Compounds - chemical synthesis Polycyclic Compounds - chemistry sulfonamides Sulfonamides - chemical synthesis Sulfonamides - chemistry Sulfones - chemistry |
| title | Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β‑Elimination of Sulfonyl Radicals to Form Polycyclic Imines |
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