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1、AdvancedOrganicSynthesisMETHODSANDTECHNIQUESRICHARDS.MONSONDEPARTMENTOFCHEMISTRYCALIFORNIASTATECOLLEGE,HAYWARDHAYWARD,CALIFORNIAACADEMICPRESSNewYorkandLondonCOPYRIGHT©1971,BYACADEMICPRESS,INC.ALLRIGHTSRESERVEDNOPARTOFTHISBOOKMAYBEREPRODUCEDINANYFORNBYPHOTOSTAT,M
2、ICROFILM,RETRIEVALSYSTEM,ORANYOTHERMEANS,WITHOUTWRITTENPERMISSIONFROMTHEPUBLISHERS.ACADEMICPRESS,INC.IllFifthAvenue,NewYork,NewYork10003UnitedKingdomEditionpublishedbyACADEMICPRESS,INC.(LONDON)LTD.BerkeleySquareHouse,LondonWlX6BALIBRARYOFCONGRESSCATALOGCARDNUMBE
3、R:75-165531PRINTEDINTHEUNITEDSTATESOFAMERICAContentsPrefacexiI.FUNCTIONALGROUPMODIFICATIONS1.ChemicalOxidationsI.ChromiumTrioxideOxidation3II.Periodate-PermanganateCleavageofOlefins5III.FreeRadicalOxidationofanAllylicPosition7IV.EpoxidationofOlefins8V.Baeyer-Vil
4、ligerOxidationofKetones9VI.LeadTetraacetateOxidationofCycloalkanols11VII.PhotolyticConversionofCyclohexanetoCyclohexanoneOxime11VIII.OxidationofEtherstoEsters12IX.PartialOxidationofanAliphaticSideChain13X.BisdecarboxylationwithLeadTetraacetate14XI.OxidationwithS
5、eleniumDioxide15References162.HydrideandRelatedReductionsI.ReductionbyLithiumAluminumHydride18II.MixedHydrideReduction20III.ReductionwithIridium-ContainingCatalysts22IV.ReductionofConjugatedAlkeneswithChromium(H)Sulfate23References243.DissolvingMetalReductionsI.
6、ReductionbyLithium-Amine25II.ReductionbyLithium-Ethylenediamine26III.Reductionofa,/MJnsaturatedKetonesbyLithium-Ammonia27IV.Reductionofa,/9-UnsaturatedKetonesinHexamethylphosphoricTriamide....28V.Reductionofana,/?-Unsaturatedy-DiketonewithZinc29References30VICON
7、TENTS4.HydroborationI.HydroborationofOlefinsasaRoutetoAlcohols32II.SelectiveHydroborationsUsingBis(3-methyl-2-butyl)borane(BMB)35III.PurificationofaMixtureofJ9-10-andJ1(9)-Octalins37References385.CatalyticHydrogenationI.HydrogenationoverPlatinumCatalyst39II.Low-
8、PressureHydrogenationofPhenolsoverRhodiumCatalysts40III.c/j-4-HydroxycyclohexanecarboxylicAcidfrom/?-HydroxybenzoicAcid41IV.3-Isoquinuclidonefrom/7-AminobenzoicAcid42
