Zorana Ferjančić, Živorad Čeković, Radomir N Saičić
{"title":"小环化合物合成中的自由基多米诺反应:含环丙烷多环的多环化","authors":"Zorana Ferjančić, Živorad Čeković, Radomir N Saičić","doi":"10.1016/S1387-1609(01)01276-2","DOIUrl":null,"url":null,"abstract":"<div><p>Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters <strong>4a–f</strong> in the presence of activated alkynes affords bicyclo〚3.1.0〛hex-2-ene derivatives <strong>5a–g</strong> in moderate yields (18–52 %). The propagation sequence comprises: intermolecular addition/5-<em>exo</em>-cyclization/3-<em>exo</em>-cyclization/β-elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 599-610"},"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)01276-2","citationCount":"1","resultStr":"{\"title\":\"Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles\",\"authors\":\"Zorana Ferjančić, Živorad Čeković, Radomir N Saičić\",\"doi\":\"10.1016/S1387-1609(01)01276-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters <strong>4a–f</strong> in the presence of activated alkynes affords bicyclo〚3.1.0〛hex-2-ene derivatives <strong>5a–g</strong> in moderate yields (18–52 %). The propagation sequence comprises: intermolecular addition/5-<em>exo</em>-cyclization/3-<em>exo</em>-cyclization/β-elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds.</p></div>\",\"PeriodicalId\":100305,\"journal\":{\"name\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"volume\":\"4 7\",\"pages\":\"Pages 599-610\"},\"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)01276-2\",\"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/S1387160901012762\",\"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/S1387160901012762","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles
Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters 4a–f in the presence of activated alkynes affords bicyclo〚3.1.0〛hex-2-ene derivatives 5a–g in moderate yields (18–52 %). The propagation sequence comprises: intermolecular addition/5-exo-cyclization/3-exo-cyclization/β-elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds.
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