有机合成学生版chapter 5.pptx

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FreeRadicalandPericyclicReactionsintheFormationofCarbon-carbonBonds5.1carbonradicalreaction5.2radicaladditionreaction5.3carbene5.4alkenemetathesis5.5theDiels-Alderreaction5.6theenereaction5.7thecopeandclaisenrearrangements

5.1CarbonRadicalReactionsThestagesinradicalreactions1initiationstepTypicalinitiators:dibenzoylperoxideAcarbonradicalisatrivalentspeciesContaininganunpairedelectroninaporbital

azobisisobutyronitrile(AIBN)偶氮二异丁腈

propagationstepterminationstep:Tworadicalcombiningwitheachothertoformacovalentbondbylosingahydrogenatom.

Syntheticallyusefulradicalreactionscoupling,additionandsubstitutionKolbeelectrolysisofcarboxylicacids.

TheUllmanncouplingofaryliodidestogivediphenyls

thePschorrsynthesisofphenanthrenes菲

TheCadiot-Chodkiewiczoxidativecouplingofterminalalkynesusingammoniacal氨的copper(1)chloride

ReductivefreeradicalcouplingprocessesThereducingofketonesbyMagnesium

Theacyloin酮醇condensationofesterswithsodium

AdditionofTMSClfavorAcyloincondensation,PreventDieckmannreaction

TheMcMurrycouplingofaldehydesandketonesusinglowoxidationtitanium

5.2RadicalAdditionReactions

tributylstannaneastheproviderofradical

Indentifytheindividualstepsinthefollowingradicalcascadecyclization:

5.3CarbenesAcarbene(R2C:)hastwononbondingelectronsasinglet单线态carbeneatriplet三线态carbene

Formationofcarbene1σ-eliminationTheeliminationofHClfromchloroformTheeliminationofI2fromdiiodomethane

2Losingnitrogenfrom3LosingCOfrom

TheSimmons-Smithmethylenationreaction

Synthesisthefollowingcompound

Arndt-Eistertreactionbasedondiazomethane

5.4AlkeneMetathesis(易位)e:couplingoftwochainsviaanalkene.

5.5TheDiels-AlderReactionHOMOLUMOLUMOHOMOSymmetryallowedSymmetryallowed[4+2]addition

NointermediateexistinthisprocessCis-formedringjunctionEndoformisthemainproduct

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