
Chemicals
p-Toluenesulphonamide(Aldrich)
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Chloramine-TistheorganiccompoundwiththeformulaCH3C6H4SO2NClNa.Boththeanhydroussaltanditstrihydrateareknown.Botharewhitepowders.Chloramine-Tisusedasareagentinorganicsynthesis.[2]Itiscommonlyusedascyclizingagentinthesynthesisofaziridine,oxadiazole,isoxazoleandpyrazoles.[3]It'sinexpensive,haslowtoxicityandactsasaoxidizingagent.Inaddition,italsoactsasasourceofnitrogenanionsandelectrophiliccations....[
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Benzylchloroformate,alsoknownasbenzylchlorocarbonateorZ-chloride,isthebenzylesterofchloroformicacid.Itcanbealsodescribedasthechlorideofthebenzyloxycarbonyl(CbzorZ)group.Initspureformitisawater-sensitiveoilycolorlessliquid,althoughimpuresamplesusuallyappearyellow.Itpossessesacharacteristicpungentodoranddegradesincontactwithwater.
ThecompoundwasfirstpreparedbyLeonidasZervasintheearly1930swhousedi...[
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Urea-hydrogenperoxideisanon-toxic,odorlesscrystallinesolid.Thisadduct,whichcontains35%ofH2O2,setsthehydrogenperoxidefreeduringitsapplication.
Urea-hydrogenperoxideinthepresenceofacatalyticamountofmagnesiumbromideefficientlyoxidizesprimaryandsecondarybenzylicalcoholsintothecorrespondingaromaticaldehydesandketones.
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o-Iodoxybenzoicacid(IBX)wasfoundtobehighlyeffectiveinoxidationsadjacenttocarbonylandbenzylicfunctionalitiestoformeitherα,β-unsaturatedcarbonylcompoundsorconjugatedaromaticcarbonylsystems.Fine-tuningofthereactionconditionsallowedremarkablyselectivetransformationswithinmultifunctionalsubstrates.
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Theuseof2-(phenylsulfonyl)-3-phenyloxaziridine(Davisreagent)orsimilaroxaziridinereagentsenablesanoxidationofenolatesgeneratedinsitufromketonesoresterstoprovideα-hydroxylatedcompounds.
MechanismoftheDavisOxidation
ThetransferofoxygenfromN-sulfonyloxaziridinestonucleophileshappensinaSN2mechanism,inwhichtheenolateanionasnucleophileattackstheoxaziridineoxygenatomtogiveahemiaminal...[
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TheKharasch–Sosnovskyreactionisamethodthatinvolvesusingacopperorcobaltsaltasacatalysttooxidizeolefinsattheallylicposition,subsequentlycondensingaperoxyester(e.g.tert-Butylperoxybenzoate)oraperoxideresultingintheformationofallylicbenzoatesoralcoholsviaradicaloxidation.[1]Thismethodisnoteworthyforbeingthefirstallylicfunctionalizationtoutilizefirst-rowtransitionmetalsandhasfoundnumerousapplicat...[
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Dimethyldioxirane(DMDO)istheorganiccompoundwiththeformula(CH3)2CO2.[1]Itisthedioxiranederivedfromacetoneandcanbeviewedasthemonomerofacetoneperoxide.Itisapowerfulselectiveoxidizingagentthatfindssomeuseinorganicsynthesis.Itisknownonlyintheformofadilutesolution,usuallyinacetone,andhencethepropertiesofthepurematerialarelargelyunknown.[2]
DMDOisnotcommerciallyavailablebecauseofchemicalinstability.DM...[
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Carbodiimide(DCC,DIC,EDCHCl)
Dicyclohexylcarbodiimide(DCC)anddiisopropylcarbodiimide(DIC)arecommonlyusedtoprepareamides,estersandacidanhydridesfromcarboxylicacids.Thesereagentscanalsoconvertprimaryamidestonitriles,whichcanbeusefulinorganicsynthesisbutisatroublesomesidereactionofasparagineandglutamineresiduesinpeptidesynthesis.Dicyclohexylurea,thebyproductformedfromDCC,isnearlyinsolubleinmostorg...[
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