Libros de Ing. Quim. Recursos para Ingenieria Quimica.

Advanced Organic Synthesis: Methods and Techniques – Richard S. Monson

Advanced Organic Synthesis: Methods and Techniques
Richard S. Monson

»DOWNLOAD THIS BOOK / DESCARGAR LIBRO AQUI

I. FUNCTIONAL GROUP MODIFICATIONS

1. Chemical Oxidations
I. Chromium Trioxide Oxidation
II. Periodate-Permanganate Cleavage of Olefins
III. Free Radical Oxidation of an Allylic Position
IV. Epoxidation of Olefins
V. Baeyer-Villiger Oxidation of Ketones
VI. Lead Tetraacetate Oxidation of Cycloalkanols
VII. Photolytic Conversion of Cyclohexane to Cyclohexanone Oxime
VIII. Oxidation of Ethers to Esters
IX. Partial Oxidation of an Aliphatic Side Chain
X. Bisdecarboxylation with Lead Tetraacetate
XI. Oxidation with Selenium Dioxide

2. Hydride and Related Reductions
I. Reduction by Lithium Aluminum Hydride
II. Mixed Hydride Reduction
III. Reduction with Iridium-Containing Catalysts
IV. Reduction of Conjugated Alkenes with Chromium (H) Sulfate

3. Dissolving Metal Reductions
I. Reduction by Lithium-Amine
II. Reduction by Lithium-Ethylenediamine
III. Reduction of a,/MJnsaturated Ketones by Lithium-Ammonia
IV. Reduction of a,/9-Unsaturated Ketones in Hexamethylphosphoric Triamide
V. Reduction of an a,/?-Unsaturated y-Diketone with Zinc

4. Hydroboration
I. Hydroboration of Olefins as a Route to Alcohols
II. Selective Hydroborations Using Bis(3-methyl-2-butyl)borane (BMB)
III. Purification of a Mixture of J9-10- and J1(9)-Octalins

5. Catalytic Hydrogenation
I. Hydrogenation over Platinum Catalyst
II. Low-Pressure Hydrogenation of Phenols over Rhodium Catalysts
III. c/j-4-Hydroxycyclohexanecarboxylic Acid from /?-Hydroxybenzoic Acid
IV. 3-Isoquinuclidone from/7-Aminobenzoic Acid
V. Homogeneous Catalytic Hydrogenation

6. The Introduction of Halogen
I. Halides from Alcohols by Triphenylphosphine—Carbon Tetrahalide
II. Halides from Alcohols and Phenols by Triphenylphosphine Dihalide
III. Allylic and Benzylic Bromination with W-Bromosuccinimide
IV. a-Bromination of Ketones and Dehydrobromination
V. Stereospecific Synthesis of /ra/w-4-Halocyclohexanols

7. Miscellaneous Elimination, Substitution, and Addition Reactions
I. Methylenecyclohexane by Pyrolysis of an Amine Oxide
II. The Wolff-Kishner Reduction
III. Dehydration of 2-Decalol
IV. Boron Trifluoride Catalyzed Hydrolysis of Nitriles
V. Bridged Sulfides by Addition of Sulfur Dichloride to Dienes
VI. Methylation by Diazomethane
VII. Oxymercuration: A Convenient Route to Markovnikov Hydration of Olefins
VIII. Esterification of Tertiary Alcohols
IX. Ketalization
X. Half-EsterificationofaDiol
XI. Substitution on Ferrocene
XII. Demethylation of Aryl Methyl Ethers by Boron Tribromide

II. SKELETAL MODIFICATIONS
8. The Diels-Alder Reaction
I. 3,6-Diphenyl-4,5-cyclohexenedicarboxylic Anhydride
II. Reactions with Butadiene
III. Catalysis by Aluminum Chloride
IV. Generation of Dienes from Diones
V. Reactions with Cyclopentadiene

9. Enamines as Intermediates
I. Preparation of the Morpholine Enamine of Cyclohexanone
II. Acylation of Enamines
III. Enamines as Michael Addition Reagents
IV. Reactions of Enamines with j3-Propiolactone
V. Reactions of Enamines with Acrolein

10. Enolate Ions as Intermediates
I. Ketones as Enolates: Car bethoxylation of Cyclic Ketones
II. Esters as Enolates: 1,4-Cyclohexanedione and Meerwein's Ester
III. Methylsulfinyl Carbanion as a Route to Methyl Ketones
IV. Cyclization with Diethyl Malonate
V. Carboxylations with Magnesium Methyl Carbonate (MMC)
VI. Alkylation of j3-Ketoesters
VII. The Robinson Annelation Reaction

11 . The Wittig Reaction
I. Benzyl-Containing Ylides
II. Alkyl Ylides Requiring «-Butyl Lithium
III. Methylsulfinyl Carbanion in the Generation of Ylides
IV. The Wittig Reaction Catalyzed by Ethylene Oxide
V. Cyclopropylidene Derivatives via the Wittig Reaction

12. Reactions of Trialkylboranes
I. Trialkylcarbinols from Trialkylboranes and Carbon Monoxide
II. Dialkylketones from Trialkylboranes and Carbon Monoxide- Water
III. The Reaction of Trialkylboranes with Methyl Vinyl Ketone and Acrolein
IV. The Reaction of Trialkylboranes with Ethyl Bromoacetate

13. Carbenes as Intermediates
I. Carbene Addition by the Zinc-Copper Couple
II. Dibromocarbenes
III. Dihalocarbenes from Phenyl(trihalomethyl)mercury Compounds

14. Ethynylation
I. Generation of Sodium Acetylide in Liquid Ammonia
II. The Generation of Sodium Acetylide in Tetrahydrofuran
III. The Generation of Sodium Acetylide via Dimsylsodium

15. Structural Isomerizations
I. Acid Catalyzed Rearrangement of Saturated Hydrocarbons
II. Photolytic Ring Contraction
III. Isomerization of 1-Ethynylcylohexanol: Three Methods
IV. Photolytic Isomerization of 1,5-Cyclooctadiene
V. Oxidative Rearrangement of /3-Diketones
VI. Base Catalyzed Rearrangement of 4-Benzoyloxycyclohexanone
VII. Allenes from 1,1-Dihalocyclopropanes by Methyllithium

16. Elimination, Substitution, and Addition Reactions Resulting in Carbon-Carbon Bond Formation
I. Carboxylation of Carbonium Ions
II. Paracyclophane via a 1,6-Hofmann Elimination
III. Diphenylcyclopropenone from Commercial Dibenzyl Ketone
IV. Phenylcyclopropane from Cinnamaldehyde
V. Conversion of Alkyl Chlorides to Nitriles in DMSO
VI. Photolytic Addition of Formamide to Olefins
VII. Intermolecular Dehydrohalogenation
VIII. Ring Enlargement with Diazomethane
IX. Conjugate Addition of Grignard Reagents
X. Dimethyloxosulfonium Methylide in Methylene Insertions
Xl. Acylation of a Cycloalkane: Remote Functionalization
XII. The Modified Hunsdiecker Reaction

17. Miscellaneous Preparations
I. Derivatives of Adamantane
II. Percarboxylic Acids
III. Diazomethane
IV. Trichloroisocyanuric Acid

Appendix 1. Examples of Multistep Syntheses
Appendix 2. Sources of Organic Reagents
Appendix 3. Introduction to the Techniques of Synthesis

»DOWNLOAD THIS BOOK / DESCARGAR LIBRO AQUI