{"title":"dow - beckwith重排的复杂例子:自由基途径生成2-氧沙比环〚3.3.0 <s:1>辛烷-3,6-二酮","authors":"David J Hart, Fabien Havas","doi":"10.1016/S1387-1609(01)01274-9","DOIUrl":null,"url":null,"abstract":"<div><p>The synthesis of 8-iodooxabicyclo〚3.2.1〛octanes from substituted benzoic acids via a reductive alkylation–halolactonization sequence is described. These iodolactones were converted to 2-oxabicyclo〚3.3.0〛octane derivatives upon treatment with either allyltri-<em>n</em>-butylstannane or tri-<em>n</em>-butylstannane via a process that involves a Dowd–Beckwith rearrangement. The scope and limitations of this process are discussed.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 591-598"},"PeriodicalIF":0.0000,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01274-9","citationCount":"1","resultStr":"{\"title\":\"Complex examples of the Dowd–Beckwith rearrangement: a free radical route to 2-oxabicyclo 〚3.3.0〛octan-3,6-diones\",\"authors\":\"David J Hart, Fabien Havas\",\"doi\":\"10.1016/S1387-1609(01)01274-9\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The synthesis of 8-iodooxabicyclo〚3.2.1〛octanes from substituted benzoic acids via a reductive alkylation–halolactonization sequence is described. These iodolactones were converted to 2-oxabicyclo〚3.3.0〛octane derivatives upon treatment with either allyltri-<em>n</em>-butylstannane or tri-<em>n</em>-butylstannane via a process that involves a Dowd–Beckwith rearrangement. The scope and limitations of this process are discussed.</p></div>\",\"PeriodicalId\":100305,\"journal\":{\"name\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"volume\":\"4 7\",\"pages\":\"Pages 591-598\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2001-07-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01274-9\",\"citationCount\":\"1\",\"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/S1387160901012749\",\"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/S1387160901012749","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Complex examples of the Dowd–Beckwith rearrangement: a free radical route to 2-oxabicyclo 〚3.3.0〛octan-3,6-diones
The synthesis of 8-iodooxabicyclo〚3.2.1〛octanes from substituted benzoic acids via a reductive alkylation–halolactonization sequence is described. These iodolactones were converted to 2-oxabicyclo〚3.3.0〛octane derivatives upon treatment with either allyltri-n-butylstannane or tri-n-butylstannane via a process that involves a Dowd–Beckwith rearrangement. The scope and limitations of this process are discussed.
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