Advanced Organic Chemistry: Part B: Reactions and SynthesisThe main theme of Part B is the description of synthetically useful reactions and the illustration of their application. We have attempted to update the material to reflect the most important advances in synthetic methodology. Because of the extensive developments in the use of organic derivatives of transition metals, as well as of silicon and tin, we have separated the organometallic material into three chapters. Chapter 7 emphasizes organolithium and organomagnesium chemistry and also considers the group lIB metals. Transition metal chemistry is discussed in Chapter 8, with emphasis on copper and palladium intermediates. In Chapter 9, the carbon-carbon bond-forming reactions of organoboranes, silanes, and stannanes are discussed. The increased importance of free-radical reactions in synthesis has led to the incorporation of a section on radical reactions into Chapter 10, in which carbocations, carbenes, and nitrenes are also discussed. Certainly a major advance in synthetic chemistry during the 1980s was the development of methods for enantioselective synthesis. We have increased the level of attention to stereochemistry in the discussion of many reactions. In areas in which new stereoselective methods have been well developed, such as in aldol condensa tions, hydroboration, catalytic reduction, and epoxidation, we discuss these methods. The final chapter discusses some of the general issues which must be addressed in multistep synthesis and provides some illustrative syntheses which can provide the basis for more detailed study of this aspect of synthetic chemistry. |
Contents
1 | |
2 | |
3 | |
6 | |
9 | |
Reactions of Carbon Nucleophiles with Carbonyl Groups | 55 |
CONTENTS | 64 |
Functional Group Interconversion by Nucleophilic Substitution | 121 |
8 | 327 |
141 | 347 |
CONTENTS | 349 |
Organometallic Compounds of Group I and II Metals | 365 |
Reactions Involving the Transition Metals | 401 |
Nucleophilic Substitution | 403 |
151 | 428 |
CarbonCarbon BondForming Reactions of Compounds | 443 |
122 | 209 |
Problems | 212 |
Reduction of Carbonyl and Other Functional Groups | 220 |
30 | 231 |
46 | 238 |
22 | 265 |
136 | 266 |
Cycloadditions Unimolecular Rearrangements and Thermal | 283 |
58 | 288 |
80 | 294 |
Photochemistry | 313 |
Concerted Reactions | 325 |
152 | 464 |
FreeRadical Reactions | 475 |
Reactions Involving Highly Reactive ElectronDeficient xi | 493 |
156 | 544 |
Aromatic Substitution Reactions | 571 |
Oxidations | 615 |
Multistep Syntheses | 678 |
General References | 747 |
763 | |
785 | |
786 | |
Other editions - View all
Common terms and phrases
acetic acylation adduct alcohols aldehydes aldol condensations alkenes allylic amides amines anion anti aromatic aryl boron bromide carbanions CARBON NUCLEOPHILES carbon-carbon carbonyl compounds carbonyl group carboxylic acids catalyst cation CH,O CH₂ CH₂O CH₂OH CH3 CH3 CH3 CH3 H Chem Chem Soc chiral chloride CO,CH CO₂C₂H CO₂CH3 CO₂H cyclic cycloaddition deprotonation derivatives dienophile DMSO double bond E. J. Corey electron ELECTROPHILIC ADDITIONS elimination ENAMINES enantioselective enol ethers epoxides esters examples formation formed FUNCTIONAL GROUPS give H CH3 H H H H,C CH H. C. Brown H₁C H₂C H₂O H3C CH3 halides halogen hydride hydrogen intermediate intramolecular ketones lithium mechanism metal methyl molecules NaBH4 NUCLEOPHILIC SUBSTITUTION OCH3 organoboranes organometallic oxidation oxygen procedure proton radical react reaction conditions REACTIONS INVOLVING reactive reagents rearrangement ring Scheme SECTION silyl sodium solvents stereochemistry stereoselectivity steric structure syn addition Synth synthesis synthetic Tetrahedron Lett transition ylides