{"title":"trans-Cycloalkenes。第三部分。非对映异构体3-取代反式环辛烯的立体化学及其反应机理","authors":"G. H. Whitham, M. Wright","doi":"10.1039/J39710000891","DOIUrl":null,"url":null,"abstract":"Three types of process are described: (i) the stereospecific addition of acetic acid to (1RS,2RS)-trans-cyclo-oct-2-enyl acetate to give cis-cyclo-octane-1,3-diol diacetate, (ii) the reaction of (1RS,2RS)- and (1SR,2RS)-trans-cyclo-oct-2-enyl methyl ethers with n-butyl-lithium to give (1RS,3RS)-3-butyl-trans-cyclo-oct-1-ene and 3-butyl-cis-cyclo-oct-1-ene, respectively, and (iii) the thermal interconversion of the diastereoisomeric acetates at 167° to give an equilibrium mixture comprising 84% of the (1RS,2RS)- and 16% of the (1SR,2RS)-form.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"20 1","pages":"891-896"},"PeriodicalIF":0.0000,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"4","resultStr":"{\"title\":\"trans-Cycloalkenes. Part III. Stereochemistry and mechanism of some reactions of diastereoisomeric 3-substituted trans-cyclo-octenes\",\"authors\":\"G. H. Whitham, M. Wright\",\"doi\":\"10.1039/J39710000891\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Three types of process are described: (i) the stereospecific addition of acetic acid to (1RS,2RS)-trans-cyclo-oct-2-enyl acetate to give cis-cyclo-octane-1,3-diol diacetate, (ii) the reaction of (1RS,2RS)- and (1SR,2RS)-trans-cyclo-oct-2-enyl methyl ethers with n-butyl-lithium to give (1RS,3RS)-3-butyl-trans-cyclo-oct-1-ene and 3-butyl-cis-cyclo-oct-1-ene, respectively, and (iii) the thermal interconversion of the diastereoisomeric acetates at 167° to give an equilibrium mixture comprising 84% of the (1RS,2RS)- and 16% of the (1SR,2RS)-form.\",\"PeriodicalId\":17245,\"journal\":{\"name\":\"Journal of The Chemical Society C: Organic\",\"volume\":\"20 1\",\"pages\":\"891-896\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1971-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"4\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of The Chemical Society C: Organic\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1039/J39710000891\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society C: Organic","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/J39710000891","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
trans-Cycloalkenes. Part III. Stereochemistry and mechanism of some reactions of diastereoisomeric 3-substituted trans-cyclo-octenes
Three types of process are described: (i) the stereospecific addition of acetic acid to (1RS,2RS)-trans-cyclo-oct-2-enyl acetate to give cis-cyclo-octane-1,3-diol diacetate, (ii) the reaction of (1RS,2RS)- and (1SR,2RS)-trans-cyclo-oct-2-enyl methyl ethers with n-butyl-lithium to give (1RS,3RS)-3-butyl-trans-cyclo-oct-1-ene and 3-butyl-cis-cyclo-oct-1-ene, respectively, and (iii) the thermal interconversion of the diastereoisomeric acetates at 167° to give an equilibrium mixture comprising 84% of the (1RS,2RS)- and 16% of the (1SR,2RS)-form.
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