Intramolecular nucleophilic carbonyl trapping of alpha-ketenyl radicals by an amino group
Free-radical carbonylation of omega-alkynylamines with tributyltin hydride gives a mixture of alpha-methylene lactams and alpha-stannylmethylene lactams. Nucleophilic addition of an internal amino group to the carbonyl group of alpha-ketenyl radicals is proposed as the cyclization step. The subseque...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2004-11 (21), p.2482-2483 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Tojino, Mami Uenoyama, Yoshitaka Fukuyama, Takahide Ryu, Ilhyong |
| description | Free-radical carbonylation of omega-alkynylamines with tributyltin hydride gives a mixture of alpha-methylene lactams and alpha-stannylmethylene lactams. Nucleophilic addition of an internal amino group to the carbonyl group of alpha-ketenyl radicals is proposed as the cyclization step. The subsequent unusual 1,4-H shift from the resulting 1-hydroxyallyl radical, followed by elimination of the beta-tributyltin radical leads to the formation of alpha-methylene lactams. |
| doi_str_mv | 10.1039/b408746a |
| format | Article |
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Nucleophilic addition of an internal amino group to the carbonyl group of alpha-ketenyl radicals is proposed as the cyclization step. 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Nucleophilic addition of an internal amino group to the carbonyl group of alpha-ketenyl radicals is proposed as the cyclization step. The subsequent unusual 1,4-H shift from the resulting 1-hydroxyallyl radical, followed by elimination of the beta-tributyltin radical leads to the formation of alpha-methylene lactams.</description><subject>Amines - chemical synthesis</subject><subject>Cyclization</subject><subject>Ethylenes - chemistry</subject><subject>Free Radicals - chemistry</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Trialkyltin Compounds - chemistry</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkEtLw0AUhQdRbK2Cv0BmJW6i88xjWYuPQsGNgq7CnelNG51k4kyy6L83pQXv5l7u-ThwDiHXnN1zJosHo1ieqRROyJTLVCVa5Z-n-1sXSSaVnpCLGL_ZOFzn52TCteYqF-mUfC3bPkDjHdrBQaDtYB36blu72lILwfh25-iIdF3dbqivKLhuC8kP9rhXAqxrCy5Ss6PQUmjq1tNN8EN3Sc6qUcCr456Rj-en98Vrsnp7WS7mq8SKrOiTVBQcANlaGyalQcFtMf7UmAOzvFozLWTKBTdopWFVlloDxnLJUAotjJAzcnvw7YL_HTD2ZVNHi85Bi36IZZoxXhRKjuDdAbTBxxiwKrtQNxB2JWflvsby8VDjfERvjp6DaXD9Dx57k39xX22Q</recordid><startdate>20041107</startdate><enddate>20041107</enddate><creator>Tojino, Mami</creator><creator>Uenoyama, Yoshitaka</creator><creator>Fukuyama, Takahide</creator><creator>Ryu, Ilhyong</creator><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>20041107</creationdate><title>Intramolecular nucleophilic carbonyl trapping of alpha-ketenyl radicals by an amino group</title><author>Tojino, Mami ; Uenoyama, Yoshitaka ; Fukuyama, Takahide ; Ryu, Ilhyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c279t-6291aae0d5b033be21c96294136e78fd05236121bec3b0f76cbabc130e3252b23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Amines - chemical synthesis</topic><topic>Cyclization</topic><topic>Ethylenes - chemistry</topic><topic>Free Radicals - chemistry</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Trialkyltin Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tojino, Mami</creatorcontrib><creatorcontrib>Uenoyama, Yoshitaka</creatorcontrib><creatorcontrib>Fukuyama, Takahide</creatorcontrib><creatorcontrib>Ryu, Ilhyong</creatorcontrib><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>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tojino, Mami</au><au>Uenoyama, Yoshitaka</au><au>Fukuyama, Takahide</au><au>Ryu, Ilhyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intramolecular nucleophilic carbonyl trapping of alpha-ketenyl radicals by an amino group</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2004-11-07</date><risdate>2004</risdate><issue>21</issue><spage>2482</spage><epage>2483</epage><pages>2482-2483</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Free-radical carbonylation of omega-alkynylamines with tributyltin hydride gives a mixture of alpha-methylene lactams and alpha-stannylmethylene lactams. Nucleophilic addition of an internal amino group to the carbonyl group of alpha-ketenyl radicals is proposed as the cyclization step. The subsequent unusual 1,4-H shift from the resulting 1-hydroxyallyl radical, followed by elimination of the beta-tributyltin radical leads to the formation of alpha-methylene lactams.</abstract><cop>England</cop><pmid>15514826</pmid><doi>10.1039/b408746a</doi><tpages>2</tpages></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2004-11 (21), p.2482-2483 |
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| language | eng |
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| source | Royal Society of Chemistry Journals Archive (1841-2007); MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines - chemical synthesis Cyclization Ethylenes - chemistry Free Radicals - chemistry Ketones - chemistry Molecular Structure Trialkyltin Compounds - chemistry |
| title | Intramolecular nucleophilic carbonyl trapping of alpha-ketenyl radicals by an amino group |
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