有机合成学生版chapter 7.pptx

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7FunctionalGroupTransformations7.1Oxidation7.2Reduction7.3Halogenation

7.1OxidationDefinition:LossofbondstoahydrogenatomorgainofbondstoanoxygenatomatacarbonatomisanoxidationTwotypes:DehydrogenationTheinsertionofoxygen

7.1.1dehydrogenationreactionThedehydrogenationofalicyclic(脂环族的)compoundtoaromaticcompoundbysulfurorselenium

2.Thedehydrogenationofketonestoα,β-unsaturatedketonesbyquinone(苯醌)

7.1.2OxidationofAlcohols1.Dehydrogenationwithchromium(Ⅵ)oxide(chromiumtrioxide)

TheresultantaldehydecanbefurtheroxidizedSeldomusedinsynthesis

SomemoreselectiveandmilderreagentsofchromiumCaution:addchromiumtopyridineslowly

2.Theuseofsilver(Ⅰ)oxide(Ag2O)tooxidizealdehydestocarboxylicacids

3.SpecificoxidationofalcoholstoaldehydesbyTrimethylamineN-oxide(Me3NO).

4.SwernoxidationreagentDimethylsulfoxidewithdioxalyl(草酰)chloride

Especiallyusefultocompoundsensitivetoacidandheat5.Dess-Martinperiodinaneoxidation

Sodiumperiodatecanchange1,2-diolsintodialdehydes.

6ManganesedioxideUsedforthespecificoxidationofallylicalcoholstounsaturatedketones.

Potassiumhexacyanoferratecatalyzed7.1.3One-electronOxidation

7.1.4OxidationofAlkenes1.Ozonolysis

2.Theepoxidation(环氧化作用)ofanalkenewithm-chloroperbenzoicacid(MCPBA)

3.Epoxidationusingtitaniumtitaniumtetraisopropoxide,t-butylhydroperoxideand(+)-or(-)-diethyltartrate(酒石酸盐)affordschiralepoxidesSharplessreagent

4.Oxidationofallylicandbenzylicpositionsbychromium(Ⅵ)oxideorchromyl(Ⅵ)chloride

7.1.5.Baeyer-Villigeroxidation

Dakinoxidationsofaromaticketones

7.2Reduction

(1)HydrogenolysisreactionsinvolvingthesubstitutionofagroupbyhydrogenThreegroupsreductiveprocesses

(2)hydrogenationreactionsinvolvingtheadditionofhydrogentoanunsaturatedsystem(3)theremovalofoxygenwithoutnecessarilyincludingtheadditionofhydrogen.

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