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Table Of Contents

1.1.1.1 Safety Glasses
1.1.1.2 Gloves
1.1.1.3 Laboratory Coats
1.1.2Material Safety Data Sheets
1.1.3Never Taste Chemicals
1.2.1Anhydrous Solvents
1.2.3Preparation and Titration of Grignard Reagents
1.2.5Generation of Zinc Reagent
1.2.6Preparation of Diazomethane
1.2.7Preparation of the Dess−Martin Reagent
1.3.2Recipes of Common Thin Layer Chromatography Stains
1.3.3Flash Chromatography
1.4 Crystallization
1.5Residual Solvent Peaks in Nuclear Magnetic Resonance
2.1.1.1Alkyl Alcohol to Alkyl Bromide
2.1.1.2Alkyl Alcohol to Alkyl Chloride
2.1.1.3Alkyl Alcohol to Alkyl Iodide
2.1.1.4Alkyl Alcohol to Azide
2.1.1.5Alkyl Alcohol (Halohydrin) to Epoxide
2.1.1.6Alcohol to Olefin via Burgess Dehydrating Reagent
2.1.1.7Alcohol to Olefin via Martin’s Sulfurane
2.1.1.8Mitsunobu Reaction
2.1.2.1.1 Traditional
2.1.2.1.2 Vinylogous Mannich
2.1.3.1 Hartwig-Buchwald Aromatic Amination
2.1.3.2 Hartwig-Buchwald Ether Formation
2.1.3.4Nucleophilic Aromatic Substitution (SNAr)
2.1.4.1Hydroboration Reaction
2.1.4.2 Michael Addition
2.2.1Alkyne Hydrolysis
2.2.2.1Epoxide Ring Opening Reactions, SN1
2.2.3.1 Ketal Formation
2.2.3.2 Enamine Formation
2.2.3.3 Imine Formation
2.2.3.4 Oxime Formation
2.2.3.5Sulfinimine Formation
2.2.3.6Thioketone Formation
2.3.1.1Acid Chloride Formation by Oxalyl Chloride
2.3.1.2Acid Chloride Formation by Phosphorous Oxychloride
2.3.1.3Acid Chloride Formation by Thionyl Chloride
2.3.1.4 Carbonyldiimidazole Activation
2.3.1.5 EDCI Activation
2.3.1.6 EEDQ Activation
2.3.1.7 Isobutylchloroformate Activation
2.3.1.8 Mukaiyama Esterification
2.3.1.9 Yamada Coupling
2.3.1.10 Yamaguchi Esterification
2.3.2.1 Fischer Esterification
2.3.2.2 TMSCHN2 Esterification
2.3.3.1 Schotten–Baumann Reaction
2.3.4.1 Dehydration to Nitrile
2.3.4.2Hydrolysis to Acid
2.3.5.1Acid Promoted
2.3.5.2Base Promoted
2.3.6.1Acid Promoted Hydrolysis to Acid
2.3.6.3Base Promoted Hydrolysis to Acid
2.3.6.4Base Promoted Hydrolysis to Amide
3.1.1 Activated Manganese Dioxide Oxidation
3.1.2.1 Pyridinium Chlorochromate
3.1.2.2 Pyridinium Dichromate
3.1.2.3 Collins Oxidation
3.1.4.1With Oxalyl Chloride (Swern)
3.1.4.2With Dicyclohexylcarbodiimide (Moffatt)
3.1.4.3With SO3.Pyridine (Parikh–Doering Oxidation)
3.1.4.4With Trifluoracetic Anhydride
3.1.4.5With Acetic Anhydride
3.1.4.7 With P2O5
3.1.4.8 With N-Chlorosuccinimide (Corey–Kim)
3.1.5 Fleming Oxidation
3.1.6.1.1 Standard
3.1.6.1.2 Schreiber–Meyer Modification
3.1.6.2. 1-Hydroxy-1,2,benziodoxol-3(1H)-one Oxidation
3.1.8Pummerer Rearrangement
3.1.10 Tetrapropylammonium Perruthenate oxidation
3.1.11Wacker Oxidation
3.2.1Jones Oxidation
3.2.2 Permanganate Oxidation
3.3.1Dimethyl Dioxirane
3.3.2 Halogenation with N-bromosuccinimide
3.3.3Jacobsen–Katsuki Epoxidation
3.3.4Oxidation of Olefin with meta-Chloroperbenzoic Acid
3.3.5 Osmium Tetroxide Dihydroxylation
3.3.6 Sharpless Asymmetric Dihydroxylation
3.3.7Sharpless Asymmetric Aminohydroxylation
3.3.8 Katsuki–Sharpless Asymmetric Epoxidation
3.3.9 Shi Epoxidation
3.3.10VO(acac)2, t-BuOOH Oxidation of Allylic Alcohols
3.4.1Baeyer–Villiger Oxidation
3.4.2 Sodium Chlorite Oxidation
3.5.1Amine to Nitrone
3.5.2Sulfide to Sulfoxide Oxidation
3.5.3Sulfide to Sulfone Oxidation
3.5.4Kagan Asymmetric Sulfur Oxidation
4.1Alcohols to Alkanes
4.2.1Reductive Amination with Sodium Triacetoxyborohydride
4.2.2Lithium Aluminum Hydride Reduction of an Amide
4.2.3Lithium Aluminum Hydride Reduction of a Nitrile
4.3.1 Lithium Aluminum Hydride
4.3.2Alane
4.3.3Borane
4.3.4.1Reduction of a Carboxylic Acid
4.3.4.2Reduction of a Lactone
4.3.5Sodium Borohydride/Boron Trifluoride Etherate
4.4.1.1Reduction of an Ester
4.4.1.2Reduction of a Weinreb Amide
4.4.1.3Reduction of a Lactone
4.4.1.4Reduction of a Nitrile
4.4.2Triethylsilane and Pd/C (Fukuyama Reduction)
4.5.1 Lithium Aluminum Hydride
4.5.2 Sodium Borohydride
4.5.3Sodium Borohydride/Cerium Trichloride (Luche Reduction)
4.5.4Zinc Borohydride
4.5.5 Diisobutylaluminum Hydride
4.5.6 Lithium tri-tert-Butoxyaluminohydride
4.5.7 L-Selectride
4.5.8 Samarium Iodide/Isopropanol (Meerwein–Pondorf–Verlag)
4.5.9 Tetramethylammonium Triacetoxyborane
4.5.10Corey–Bakshi–Shibata Reduction
4.5.11 R-Alpine Borane (Midland Reduction)
4.5.12Baker’s Yeast
4.6.1.1 Traditional
4.6.1.2 Myers’ Modification
4.6.2Desulfurization with Raney Nickel
4.6.3Reduction of Tosylhydrazones with Sodium Cyanoborohydride
4.6.4Zinc Amalgam (Clemmensen Reduction)
4.6.5Ionic Hydrogenation with Triethyl Silane and Boron Trifluoride
4.6.6Shapiro Reaction
4.7.1Tributyltin Hydride
4.7.2 Trialkylsilanes
4.8.1 Pd/C, H2
4.8.2Lindlar’s Catalyst
4.8.3Diimide
4.8.4 Sodium Bis(2-methoxyethoxy(aluminum hydride))
4.8.5 Lithium/Ammonia (Birch Reduction)
4.9.1Reduction of a Nitro Group to an Amine Using Ammonium Formate
4.9.2 Sodium Borohydride/Nickel Dichloride
4.9.3 Staudinger Reaction
5.1.1.1.1Evans Aldol (With Two Oxazolidinone Chiral Auxillaries)
5.1.1.1.2 Masamune Aldol
5.1.1.2.1 Standard
5.1.1.2.2 Asymmetric Mukaiyama
5.1.1.3Crimmins’ Asymmetric Aldol (Thione Chiral Auxillary)
5.1.2Asymmetric Deprotonation
5.1.3Baylis–Hillman Reaction
5.1.4Benzoin Condensation
5.1.5Brown Asymmetric Crotylation
5.1.6Claisen Condensation
5.1.7.1Lower Order Cuprates
5.1.8Dieckmann Condensation
5.1.9.1.1 Norephedrine-Derived Oxazolidinone
5.1.9.1.2 Valinol-Derived Oxazolidinone
5.1.9.2 Myers’ Asymmetric Alkylation
5.1.10Friedel–Crafts Reaction
5.1.11Grignard Reaction (Organomagnesium Reagents)
5.1.12.2Jeffrey’s Ligandless Conditions
5.1.12.3Heck Reactions of Aryl Chlorides (Fu Modification)
5.1.13Henry Reaction (Nitro Aldol)
5.1.14.1 Standard Hiyama
5.1.14.2Denmark Modification
5.1.14.3Fu Modification (Room Temperature Coupling)
5.1.15Keck Stereoselective Allylation
5.1.16.1With a Palladium Catalyst
5.1.16.2With a Nickel Catalyst
5.1.17.1 Standard
5.1.17.2 Fu Modification
5.1.18Nozaki–Hiyama–Kishi Reaction (Organochromium Reagents)
5.1.19Organocerium Reagent Addition to a Carbonyl
5.1.20.1.1 With n-BuLi
5.1.20.1.2. With t-BuLi
5.1.20.2.1 Alkynes
5.1.20.2.2. Ortho-metallations
5.1.21Reformatsky Reaction (Organozinc)
5.1.22Roush Crotylation
5.1.23.1 Traditional
5.1.23.2Denmark’s Version Using a Chiral Bis-phosphoramide
5.1.24Schwartz’s Reagent
5.1.25Shapiro Reaction
5.1.26Sonogashira Coupling
5.1.27Stille Reaction
5.1.28Stille–Kelly Reaction
5.1.29.1.1Formation of the Boronic Acid
5.1.29.1.2Standard Suzuki
5.1.29.1.3Fu Modification
5.1.29.2.1Formation of a Boronic Ester: Halogen–Lithium Exchange
5.1.29.2.2 Standard Suzuki–Miyaura
5.1.29.3.1 Formation of an Organotrifluoroborate
5.1.29.3.2 Standard Suzuki
5.1.30Tsuji–Trost Reaction
5.2.1.1Formation of a Dibromoalkene
5.2.1.2Formation of a Methylalkyne
5.2.2 Corey–Peterson Olefination
5.2.3.1Standard Horner–Wadsworth–Emmons
5.2.3.2Masamune–Roush Modification of the Horner–Wadsworth–Emmons Reaction
5.2.3.3Still–Gennari Modification of the Horner–Wadsworth–Emmons Reaction
5.2.3.4Ando Modification of the Horner–Wadsworth–Emmons Reaction
5.2.4Julia Coupling
5.2.5 Knoevenagel Condensation
5.2.6 McMurry Coupling
5.2.7.1 Lombardo–Takai
5.2.7.2 Petasis Reagent
5.2.7.3 Tebbe Reagent
5.2.7.4 Wittig
5.2.8.1Schrock’s Catalyst for Ring Closing Metathesis
5.2.8.2.1First Generation Grubbs’catalyst
5.2.8.2.2bSecond Generation Grubbs’ Catalyst: Diene Formation from an Enyne
5.2.8.3Hoyveda–Grubbs’ Catalyst (Intermolecular Reaction)
5.2.9Peterson Olefination
5.2.10Takai Olefination
5.2.11.1 Unstabilized Ylides
5.2.11.2 Stabilized Ylides
5.3.1Diels–Alder Reaction Using Danishefsky’s Diene
5.3.2Hetero-Diels-Alder Reaction Using Rawal’s Diene
5.3.3Simmons−Smith Reaction
6.1.1 Acetate
6.1.2 Acetonide
6.1.3Benzyl ether
6.1.4 para-Methoxybenzyl
6.1.5 Methyl ether
6.1.6 Methoxymethylene ether
6.1.7 tert-Butyldiphenylsilyl ether
6.1.8Tetrahydropyran
6.2.4 Carbobenzyloxy
6.2.5 9-Fluorenylmethyl carbamate
6.2.6Phthaloyl
6.2.7 Sulfonamide
6.2.8Trifluoroacetyl
6.3.41,3-Dithiane
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Modern Organic Synthesis in the Laboratory

Modern Organic Synthesis in the Laboratory

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Published by Farooq Muhammad
Modern Organic Synthesis in the Laboratory
Modern Organic Synthesis in the Laboratory

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Published by: Farooq Muhammad on Mar 17, 2013
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05/14/2014

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