Josefina Quirante , Faïza Diaba , Xavier Vila , Josep Bonjoch , Elena Lago , Elies Molins
{"title":"三氯乙酰胺6-外显基环化反应中n取代基由苄基变为α-甲基苄基的意外过程","authors":"Josefina Quirante , Faïza Diaba , Xavier Vila , Josep Bonjoch , Elena Lago , Elies Molins","doi":"10.1016/S1387-1609(01)01261-0","DOIUrl":null,"url":null,"abstract":"<div><p>Radical cyclization of <em>N</em>-(α-methyl)benzyl substituted trichloroacetamides upon α,β-unsaturated nitriles has been studied. Tributyltin hydride treatment of trichloroacetamides <strong>5a</strong> and <strong>5b</strong> gives morphan derivatives (<strong>1</strong> and <strong>2</strong>), through a 6-<em>exo</em>-trig radical cyclization, and unexpectedly normorphans <strong>6</strong> and <strong>7</strong> as a result of a stereoespecific process in which the stereogenic benzylic carbon undergoes a configurational inversion.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 513-521"},"PeriodicalIF":0.0000,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01261-0","citationCount":"2","resultStr":"{\"title\":\"An unexpected course in the 6-exo radical cyclizations of trichloroacetamides on changing the N-substituent from benzyl to α-methylbenzyl\",\"authors\":\"Josefina Quirante , Faïza Diaba , Xavier Vila , Josep Bonjoch , Elena Lago , Elies Molins\",\"doi\":\"10.1016/S1387-1609(01)01261-0\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Radical cyclization of <em>N</em>-(α-methyl)benzyl substituted trichloroacetamides upon α,β-unsaturated nitriles has been studied. Tributyltin hydride treatment of trichloroacetamides <strong>5a</strong> and <strong>5b</strong> gives morphan derivatives (<strong>1</strong> and <strong>2</strong>), through a 6-<em>exo</em>-trig radical cyclization, and unexpectedly normorphans <strong>6</strong> and <strong>7</strong> as a result of a stereoespecific process in which the stereogenic benzylic carbon undergoes a configurational inversion.</p></div>\",\"PeriodicalId\":100305,\"journal\":{\"name\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"volume\":\"4 6\",\"pages\":\"Pages 513-521\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2001-06-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01261-0\",\"citationCount\":\"2\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1387160901012610\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1387160901012610","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
An unexpected course in the 6-exo radical cyclizations of trichloroacetamides on changing the N-substituent from benzyl to α-methylbenzyl
Radical cyclization of N-(α-methyl)benzyl substituted trichloroacetamides upon α,β-unsaturated nitriles has been studied. Tributyltin hydride treatment of trichloroacetamides 5a and 5b gives morphan derivatives (1 and 2), through a 6-exo-trig radical cyclization, and unexpectedly normorphans 6 and 7 as a result of a stereoespecific process in which the stereogenic benzylic carbon undergoes a configurational inversion.
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