An extensive update of the classic reference on organic reactions in water Published almost a decade ago, the first edition has served as the guide for research in this burgeoning field. Due to the cost, safety, efficiency, and environmental friendliness of water as a solvent, there are many new applications in industry and academic laboratories. More than forty percent of this extensively updated second edition covers new reactions. For ease of reference, it is organized by functional groups. A core reference, Comprehensive Organic Reactions in Aqueous Media, Second Edition: Provides the most comprehensive coverage of aqueous organicreactions available Covers the basic principles and theory and progresses to applications Includes alkanes, alkenes, aromatics, electrophilic substitutions, carbonyls, alpha, beta-unsaturated carbonyls, carbon-nitrogen bonds, organic halides, pericyclic reactions, photochemical reactions, click chemistry, and multi-step syntheses? Provides examples of applications in industry This is the premier reference for chemists and chemical engineers in industry or research, as well as for students in advanced-level courses.

Chao-Jun Li, PhD, is Professor at McGill University in Canada. Professor Li began teaching at Tulane University in 1994 and received an NSF CAREER Award for work done from 1998–2002, the Outstanding Young Oversea Scientist Award from the NSFC in 2001, and the U.S. Presidential Green Chemistry Challenge Award in Academia for 2001. Dr. Li moved to McGill University in 2003 and received a Canada Research Chair in Green Chemistry (Tier I). He coauthored the popular first edition of Organic Reactions in Aqueous Media (Wiley).

Tak-Hang Chan, PhD, is Professor Emeritus at McGill University in Canada and Chair Professor of Organic Chemistry at the Hong Kong Polytechnic University in Hong Kong. In 1993, Professor Chan received the prestigious R.U. Lemieux Award of the Canadian Society of Chemistry. A pioneer in green chemistry, he is a Fellow of the Royal Society of Canada and holds Honorary Professorships at Academia Sinica, Peking University, and Lanzhou University. He was coauthor of the first edition.

Preface to the Second Edition	p. XV
Introduction	p. 1
The Structure and Forms of Water	p. 3
Properties of Water	p. 4
Solvation	p. 6
Hydrophobic Effect	p. 6
Salt Effect	p. 8
Water Under Extreme Conditions	p. 9
References	p. 13
Alkanes	p. 15
Oxygenation of Alkanes	p. 15
Halogenation of Alkanes	p. 20
Formation of Carbon-Carbon Bonds	p. 20
D/H Exchange of Alkanes in Water	p. 21
References	p. 22
Alkenes	p. 25
Reduction	p. 25
Hydrogenation	p. 25
Electrophilic Additions	p. 28
Reaction with Halogen	p. 28
Reaction with Hydrogen Halides	p. 28
Addition of Water	p. 29
Oxymercuration/Oxymetalation	p. 29
Epoxidation	p. 30
Dihydroxylation and Hydroxylamination	p. 35
Wacker's Oxidation	p. 40
Oxidative C=C Bond Cleavage	p. 43
C-C Bond Formations	p. 46
Radical Reactions of Alkenes	p. 47
Radical Polymerization of Alkenes	p. 47
Radical Additions	p. 48
Radical Cyclization	p. 49
Carbene Reactions	p. 50
The Generation of Carbenes in Aqueous Medium	p. 50
The Stability of Carbenes	p. 50
The Reaction of Carbenes with Alkenes in Aqueous Medium	p. 51
Alkene Isomerization	p. 52
Transition-Metal Catalyzed C-C Formation Reactions	p. 53
Polymerizations	p. 53
Heck Reactions and Related Vinylation/Arylation	p. 54
Hydrovinylation	p. 56
Reaction with Arenes	p. 56
Hydroformylation	p. 57
Reaction with Alkynes	p. 58
Carbonylation	p. 60
Cycloaddition Reactions of Alkenes	p. 60
Olefin Metathesis	p. 60
Ring-Opening Metathesis Polymerization (ROMP)	p. 61
Ring-Closing Metathesis (RCM)	p. 62
Reaction of Allylic C-H Bond	p. 64
Allylic Oxidation	p. 64
C-C Bond Formations	p. 65
References	p. 66
Alkynes	p. 77
Reaction of Terminal Alkynes	p. 77
Alkyne Oxidative Dimerization	p. 77
Alkyne-Alkyne Addition	p. 78
Reaction of Alkynes with Organic Halides	p. 81
Reaction of Alkynes with Carbonyl Compounds	p. 93
Reaction of Alkynes with C=N Compounds	p. 94
Conjugate Addition with Terminal Alkynes	p. 97
Additions of C[Xi]C bonds	p. 98
Reduction	p. 98
Addition of Water	p. 98
Addition of Alcohols and Amines	p. 100
Hydrosilation and Hydrometalations	p. 102
Addition of Aryls	p. 104
Carbonylation of Internal Alkynes	p. 107
Other Additions to Alkynes	p. 109
Transition-Metal Catalyzed Cycloadditions	p. 109
Pauson-Khand-Type Reactions	p. 109
[2 + 2 + 2] Cyclotrimerization	p. 111
[2 + 2 + 2] Alkyne-Nitrile Cyclotrimerization	p. 114
[3 + 2] 1,3-Dipolar Cycloaddition	p. 114
[4 + 2] Cycloaddition	p. 118
[5 + 2] Cycloaddition	p. 119
Other Cycloadditions	p. 119
Other Reactions	p. 121
References	p. 121
Alcohols, Phenols, Ethers, Thiols, and Thioethers	p. 129
Oxidation of Alcohols	p. 129
Diol Cleavage	p. 134
Substitutions/Elimination	p. 134
Addition of Alcohols, Phenols, and Thiols to Alkene and Alkyne Bonds	p. 137
Addition of Alcohols to C=O Bonds: Esterification and Acetal Formations	p. 137
Reaction of Ethers and Cyclic Ethers	p. 138
Ethers and Cyclic Ethers	p. 138
Reactions of Epoxides in Water and "Click Chemistry"	p. 139
Reaction of Sulfur Compounds	p. 141
Oxidation of Thiols and Thioethers	p. 141
Reduction of Disulfides	p. 142
Native Chemical Ligation for Peptide Synthesis	p. 143
Other Reactions	p. 143
References	p. 144
Organic Halides	p. 151
General	p. 151
Redaction	p. 151
Elimination Reactions	p. 154
Nucleophilic Substitutions	p. 154
Substituted by Heteroatoms	p. 154
Carbon-Carbon Bond Formations	p. 158
Reductive Coupling	p. 161
Wurtz-Type Coupling	p. 161
Ullmann-Type Coupling and Related Reactions	p. 163
Carbonylation of Organic Halides	p. 164
Carbonylation of Alkyl Halides	p. 164
Carbonylation of Allylic and Benzylic Halides	p. 165
Carbonylation of Aryl Halides	p. 165
Transition-Metal Catalyzed Coupling Reactions	p. 166
The Heck Coupling	p. 166
The Suzuki Coupling	p. 167
The Stille Coupling	p. 172
Other Transition-Metal Catalyzed Couplings	p. 173
References	p. 174
Aromatic Compounds	p. 181
General	p. 181
Substitution Reactions	p. 182
Electrophilic Substitutions	p. 182
Friedel-Crafts C-C Bond Formations	p. 183
Other Substitution Reactions	p. 189
Oxidation Reactions	p. 190
Simple Oxidation	p. 190
Oxidative Coupling	p. 191
Reductions	p. 192
References	p. 193
Aldehdye and Ketones	p. 197
Reduction	p. 197
Hydrogenation	p. 197
Other Reductions	p. 198
Oxidation	p. 204
Nucleophilic Addition: C-C Bond Formation	p. 206
Allylation	p. 206
Propargylation	p. 238
Cyclopentadienylation	p. 242
Benzylation	p. 242
Arylation/Vinylation	p. 244
Alkynylation	p. 246
Alkylation	p. 246
Reformatsky-Type Reaction	p. 246
Direct Aldol Reaction	p. 248
Mukaiyama Aldol Reaction	p. 252
Hydrogen Cyanide Addition	p. 258
Wittig Reactions	p. 259
Pinacol Coupling	p. 261
Other Reactions (Halogenation and Oxidation of [alpha]-H)	p. 262
References	p. 263
Carboxylec Acids and Derivatives	p. 279
General	p. 279
Reaction of [alpha]-Hydrogen	p. 279
Reduction	p. 279
Carboxylic Acids	p. 280
Esterification/Amidation	p. 280
Decarboxylation	p. 287
Carboxylic Acid Derivatives	p. 287
Esters and Thiol Esters	p. 287
Acid Halides and Anhydrides	p. 288
Amides	p. 289
Nitriles	p. 289
References	p. 290
Conjugated Carbonyl Compounds	p. 293
Reduction	p. 293
Hydrogenation	p. 293
Asymmetric Hydrogenation	p. 295
Reduction by Other Methods	p. 296
Epoxidation, Dihydroxylation, Hydroxyamination	p. 297
Conjugate Addition: Heteroatom	p. 298
C-C Bond Formation	p. 301
Addition of Hydrogen Cyanide	p. 302
Addition of [alpha]-Carbonyl Compounds	p. 302
Addition of Allyl Groups	p. 304
Addition of Alkyl Groups	p. 305
Addition of Vinyl and Aryl Groups	p. 307
Addition of Alkynyl Groups	p. 310
Other Conjugate Additions	p. 310
Other Reactions	p. 310
Reductive Coupling	p. 310
Baylis-Hillman Reactions	p. 311
[gamma]-Addition of Alkynoates	p. 314
References	p. 315
Nitrogen Compounds	p. 321
Amines	p. 321
Alkylation	p. 321
Diazotization and Nitrosation	p. 322
Oxidation	p. 323
Reaction with Carbonyl Compounds	p. 326
Imines	p. 327
Reductions	p. 327
Nucleophilic Additions	p. 329
Reductive Coupling	p. 342
Diazo Compounds	p. 343
Substitution	p. 343
Reduction	p. 343
Cyclopropanation	p. 344
Coupling Reaction	p. 346
Azides	p. 346
Substitution	p. 346
Click Chemistry	p. 347
Nitro Compounds	p. 349
References	p. 349
Pericyclic Reactions	p. 355
Introduction	p. 355
Diels-Alder Reactions	p. 357
Lewis-Acid Catalysis	p. 360
Asymmetric Diels-Alder Reactions	p. 367
Theoretical and Mechanistic Studies	p. 371
Synthetic Applications	p. 374
Hetero-Diels-Alder Reactions	p. 382
Asymmetric Hetero-Diels-Alder Reactions	p. 388
Other Cyclization Reactions	p. 390
Sigmatropic Rearrangements	p. 392
Claisen Rearrangements	p. 392
Cope Rearrangements	p. 397
Photochemical Cycloaddition Reactions	p. 398
References	p. 399
Index	p. 409
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