Carbocation Chemistry

Jie Jack Li earned his Ph.D. in organic chemistry in 1995 at Indiana University. After a stint as a postdoctoral fellow at MIT, he worked as a medicinal chemist at Pfizer and Bristol-Myers Squibb from 1997 to 2012. Since then he has been an Associate Professor of Chemistry at the University of San Francisco teaching organic and medicinal chemistry. He has published 23 books ranging from organic and medicinal chemistry, to the history of drug discovery.

• Chapter 1. Introduction Nomenclature, Structure, and StabilityGeneration of CarbocationsThe Non-Classical Ion ControversyElectrophilic Addition to AlkenesElectrophilic Aromatic SubstitutionElimination reactionsRearrangement Reactions of CarbocationsReferencesChapter 2. Nucleophilic Aliphatic Substitution – SN1 Introduction-Activated Alcohols—Brønsted Acids-Activated Alcohols—Lewis AcidsAlkylation of Aldehydes and KetonesGlycosylation Friedel–Crafts Alkylation and Acylation Electrophilic Fluorination Using Fluoronium IonMiscellaneous SN1-related ReactionsReferencesChapter 3. Nucleophilic Aliphatic Substitution – SN2 Construction of Quaternary Stereogenic CentersSulfur ChemistryOrganometallic ChemistryMacrocyclizationGlycosylationNucleoside AnaloguesN-AlkylationCyclotetraphosphazenesConformationally Locked Tetrahydropyran RingThe Ionic Liquid EffectSilver ChemistryReferencesChapter 4. Electrophilic Addition to Alkenes IntroductionCyclopropanationHydroboration/OxidationThe Pauson–Khand ReactionPrins ReactionSchmidt ReactionHalogenationOxymercuration/ReductionEpoxidationGold-Catalyzed Alkyne HydrationConclusionReferencesChapter 5. Electrophilic Aromatic Substitution IntroductionNitrationHalogenationFriedel–Crafts AlkylationFriedel–Crafts AcylationApplications of Friedel–Crafts Reaction on Total SynthesisMiscellaneous Electrophilic Aromatic Substitution ReactionsReferencesChapter 6. Fragmentation and Rearrangement Reactions Claisen RearrangementsCope RearrangementsCope RearrangementsAldehyde (or Ketone) Formation RearrangementsCarboxylic Acid Formation RearrangementsAlcohol Formation Rearrangements Amine Formation Rearrangement AmidesHydrocarbon RearrangementsOxacyclic, Carbocyclic, Oxazoles, Tetrahydrapuran and Tetrahydropuran Formation RearrangementsRearrangements resulting in less common functional groups FragmentationsReferences