Parashar R.K. Reaction Mechanisms in Organic Synthesis

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размер 15.04 МБ
добавлен 21 ноября 2011 г.

Wilеy, 2009, 372 pages
Content
Synthetic Strategies
An introduction to organic synthesis
Retrosynthetic analysis (disconnection approach)
Umpolung strategy
Atom economy
Selectivity
Chemoselectivity
Regioselectivity
Stereoselectivity
Asymmetric synthesis or chiral synthesis
Protecting groups
Common hydroxyl protecting groups
Common diols protecting groups
Common amine protecting groups
Common carbonyl protecting groups
Common carboxylic acid protecting groups
Common arenesulfonic acid protecting groups
Common alkyne protecting groups
Reactive Intermediates
Carbocations
Structure and stability of carbocations
Generation of carbocations
Reactions of carbocations
Non-classical carbocations
Carbanions
Structure and stability of carbanions
Generation of carbanions
Reactions of carbanions
Free radicals
Structure and stability of free radicals
Generation of free radicals
Radical ions
Reactions of radicals
Carbenes
Structure and stability of carbenes
Generation of carbenes
Reactions of carbenes
Nitrenes
Structure and stability of nitrenes
Generation of nitrenes
Reactions of nitrenes
Benzynes
Generation of benzynes
Reactions of benzynes
Stabilized Carbanions, Enamines and Ylides
Stabilized carbanions
Reaction of stabilized carbanions (enolates) with alkyl halides (enolate alkylation)
Reaction of stabilized carbanions with carbonyl compounds
Conjugate addition of enolate to ?,?-unsaturated carbonyl compounds
Reaction of enolates with iminium ions or imines
Enamines
Ylides
Formation of ylides
Reactions of ylides
Asymmetric ylide reactions
Carbon—Carbon Double Bond Forming Reactions
Introduction
Elimination reactions
?-Eliminations
Unimolecular syn-eliminations
Reactions from epoxides, thionocarbonates and episulfides
Alkenation (alkylidenation) of carbonyl compounds
Wittig reactions
Julia alkenation and modified Julia alkenation (Julia—Коcienski alkenation)
Peterson reaction
Use of titanium-based reagents
Use of Zinc (Zn) and Zirconium (Zr) reagents for the alkenation of ketones and aldehydes
Bamford—Stevens reaction and Shapiro reaction
Barton—Kellogg reaction
Catalytic aldehyde and ketone alkenation
Reduction of alkynes
Transition Metal-Mediated Carbon-Carbon Bond Forming Reactions
Carbon-carbon bond forming reactions catalyzed by transition metals
Heck reaction
Allylic substitutions
Cu-and Ni-catalyzed couplings
Transition metal-catalyzed coupling of organometallic reagents with organic halides and related electrophiles
Coupling of Grignard reagents
Coupling of organostannanes
Coupling of organoboranes
Coupling of organosilanes
Coupling of organocopper reagents
Coupling of organozinc compounds
Reduction
Reduction of carbon-carbon double bond
Catalytic hydrogйnation
Hydrogen transfer reagents
Reduction of acetylenes
Catalytic hydrogenation
Dissolving metals
Metal hydrides
Hydroboration-protonation
Reduction of benzene and derivatives
Catalytic hydrogenation
Birch reduction
Reduction of carbonyl compounds
Catalytic hydrogenation
Metal hydrides
Metal and proton source
Hydrogen transfer reagents
Reduction of ?,?-unsaturated aldehydes and ketone
Catalytic hydrogenation
Hydride reagents
Dissolving metals
Reduction of nitro, N-oxides, oximes, azides, nitriles and nitroso compounds
Catalytic hydrogenation
Metal hydrides
Metal and proton source
Triphenylphosphine
Hydrogenolysis
Oxidation
Oxidation of alcohols
Chromium(VI)
Potassium permanganate
Manganese dioxide (MnO2)
Dimethylsulfoxide-mediated oxidations
Dess-Martin periodinane (DMP)
Terra-n-propylammonium perruthenate (TPAP)
Silver oxide and silver carbonate
Oppenauer oxidation
Oxidation of aldehydes and ketones
Oxidation of phenols
Epoxidation
Dihydroxylation
Aminohydroxylation
Oxidative cleavage of C-C double bonds
Ozonolysis
Glycol cleavage
Oxidation of anilines
Dehydrogenation
Allylic or benzylic oxidation
Oxidation of sulfides
Oxidation of aliphatic side chains attached to aromatic ring
Pericyclic Reactions
Important classes of pericyclic reactions
Cycloaddition reactions
Electrocyclic reactions
Sigmatropic rearrangements
Ene reactions
Other classes of pericyclic reactions
Theoretical explanation of pericyclic reactions
MOs and their symmetry properties
Suprafacial and antarafacial
Conservation of orbital symmetry
Cycloaddition reactions
[4+2]-Cycloaddition reactions
[2+2]-Cycloaddition reactions
1,3-Dipolar additions
Theoretical explanation
Electrocyclic reactions
Theoretical explanation
General rules for electrocyclic reactions
Sigmatropic rearrangements
Analysis of sigmatropic rearrangements
Carbon shift
Ene reactions
Selection rules

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