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16.14
EpoxidesinBiologicalProcesses
arecommonareinvolvedinnumerousbiologicalprocessesNaturallyOccurringEpoxides
enzyme-catalyzedoxygentransferfromO2toalkeneenzymesarereferredtoasmonooxygenasesBiosynthesisofEpoxides++CC++O2H+CCONADHH2O+NAD+enzyme
thisreactionisanimportantstepinthebiosynthesis
ofcholesterolExample:biologicalepoxidationofsqualeneO2,NADH
monoxygenaseO
16.15
PreparationofSulfides
preparedbynucleophilicsubstitution(SN2)PreparationofRSR+RXSR–???
?????RSR??CH3CHCHCH2ClNaSCH3methanolCH3CHCHCH2SCH3
16.16
OxidationofSulfides:
SulfoxidesandSulfones
eitherthesulfoxideorthesulfonecanbeisolated
dependingontheoxidizingagentandreaction
conditionsOxidationofRSR??RSR????RSRO?
????
?–+RSRO?
????
?–++O?
??
???–sulfidesulfoxidesulfone
Example??SCH3??NaIO4??SCH3O?
????
?–+ Sodiummetaperiodateoxidizessulfidestosulfoxidesandnofurther.(91%)water
ExampleH2O2 1equivofH2O2oraperoxyacidgivesasulfoxide,2equivgiveasulfone(74-78%)(2equiv)??SCH??CH2SCHO?
????
?–++CH2O?
??
???–
16.17
AlkylationofSulfides:
SulfoniumSalts
productisasulfoniumsaltSulfidescanactasnucleophiles+RXSR?
???RSR??RR+X–
ExampleCH3(CH2)10CH2SCH3CH3ICH3(CH2)10CH2SCH3CH3+I–
Section16.18
SpectroscopicAnalysisofEthers
C—Ostretching:1070and1150cm-1(strong)InfraredSpectroscopy
FrancisA.Carey,OrganicChemistry,FourthEdition.Copyright?2000TheMcGraw-HillCompanies,Inc.Allrightsreserved.200035003000250010001500500Wavenumber,cm-1Figure16.8InfraredSpectrumofDipropylEtherC—O—CCH3CH2CH2OCH2CH2CH3
H—C—OprotonisdeshieldedbyO;rangeis
ca.d3.3-4.0ppm.1HNMRCH3CH2CH2OCH2CH2CH3d0.8ppmd0.8ppmd1.4ppmd3.2ppm
01.02.03.04.05.06.07.08.09.010.0Chemicalshift(d,ppm)CH3CH2CH2OCH2CH2CH3Figure16.9(page642)
68.0ppmCarbonsofC—O—Cappear
intheranged57-87ppm.26.0ppm13CNMRO
Simpleethershavetheirabsorptionmaximumatabout185nmandaretransparenttoultravioletr
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