Essential Reagents for Organic Synthesis

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From Boron Trifluoride to Zinc, the 52 most widely used reagents in organic synthesis are described in this unique desktop reference for every organic chemist. The list of reagents contains classics such as N-Bromosuccinimide (NBS) and Trifluoromethanesulfonic Acid side by side with recently developed ones like Pinacolborane and Tetra-n-propylammonium Perruthenate (TPAP).

For each reagent, a concise article provides a brief description of all important reactions for which the reagent is being used, including yields and reaction conditions, an overview of the physical properties of the reagent, its storage conditions, safe handling, laboratory synthesis and purification methods. Advantages and disadvantages of the reagent compared to alternative synthesis methods are also discussed.

Reagents have been hand-picked from among the 5000 reagents contained in EROS, the Encyclopedia of Reagents for Organic Synthesis. Every organic chemist should be familiar with these key reagents that can make almost every reaction work.

Preface ix

Short Note on InChIs and InChIKeys xi

General Abbreviations xiii

Bis(dibenzylideneacetone)palladium(0) 2

9-Borabicyclo[3.3.1]nonane Dimer 17

Boron Trifluoride Etherate 27

N-Bromosuccinimide 43

n-Butyllithium 54

N,N[1]-Carbonyl Diimidazole 72

Cerium(IV) Ammonium Nitrate 80

m-Chloroperbenzoic Acid 87

N-Chlorosuccinimide 98

Chlorotrimethylsilane 108

Chlorotris(triphenylphosphine)-rhodium(I) 121

(Diacetoxyiodo)benzene 136

Diazomethane 145

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 152

Diisobutylaluminum Hydride 164

4-Dimethylaminopyridine 170

Dimethyldioxirane 176

1-Ethyl-3-(3[1]-dimethylaminopropyl) carbodiimide Hydrochloride 184

N-Iodosuccinimide 188

Iodotrimethylsilane 194

2-Iodoxybenzoic Acid 206

Lithium Aluminum Hydride 212

Lithium Diisopropylamide 224

Lithium Naphthalenide 241

Manganese Dioxide 248

Osmium Tetroxide 264

Oxalyl Chloride 283

Oxalyl Chloride–Dimethylformamide 288

Ozone 290

Pinacolborane 306

Potassium Hexamethyldisilazide 313

Potassium Monoperoxysulfate 334

Potassium tert-Butoxide 353

Ruthenium(II), Tris(2,2[1]-bipyridine-κN1,κN1[1])-, (OC-6-11)- 370

Samarium(II) Iodide 378

Scandium Trifluoromethanesulfonate 388

Sodium Azide 398

Sodium Borohydride 406

Sodium Cyanoborohydride 419

Sodium Hexamethyldisilazide 428

Sodium Hydride 438

Sodium Periodate 447

Tetrabutylammonium Fluoride 458

Tetrakis(triphenylphosphine)-palladium(0) 467

Tetra-n-propylammonium Perruthenate 476

p-Toluenesulfonyl Chloride 480

Triethylsilane 489

Trifluoromethanesulfonic Acid 498

Trifluoromethanesulfonic Anhydride 507

Trimethylsilyl Trifluoromethanesulfonate 524

Trimethylsilyldiazomethane 543

Zinc–Acetic Acid 554

List of Contributors 000

Subject Index 000

Professor Philip L. Fuchs from Purdue University, West Lafayette, USA.

Professor André B. Charette from Montréal University, Canada.

Professor Tomislav Rovis from Colorado State University, Fort Collins, USA.

Professor Jeffrey W. Bode from the ETH - Swiss Institute of Technology, Zurich, Switzerland.
Are the current editors of EROS, the Encyclopedia of Reagents for Organic Synthesis.
EROS was founded by Leo Paquette in 1995. Since then it has grown into the largest collection of its kind, covering close to 5,000 different organic-chemical reagents and catalysts.