标题: Introduction to strategies for organic synthesis+pdf+60+长期有效 [打印本页] 作者: small 时间: 2012-11-23 14:44 标题: Introduction to strategies for organic synthesis+pdf+60+长期有效 本帖最后由 small 于 2012-11-23 14:50 编辑
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Preface
PART I Synthetic Toolbox 1: Retrosynthesis and Protective Groups 1
CHAPTER 1.1 Retrosynthetic Analysis 3
Retrosynthesis by Functional Group Interconversion (FGI) 4
Retrosynthesis by Making a Disconnection 6
CHAPTER 1.2 Protective Groups 11
Protection of Ketones and Aldehydes 12
Protection of Alcohols 12
Protection of Carboxylic Acids 16
Protection of Amines 17
Part I Problems Protective Groups 19
PART II Synthetic Toolbox 2: Overview of Organic Transformations 21
CHAPTER 2.1 Nucleophiles and Electrophiles 23
Common Nucleophiles 23
Common Electrophiles 26
CHAPTER 2.2 Oxidation and Reduction Reactions 27
Overview of Oxidations and Reductions 27
Common Oxidation Reactions and Oxidizing Agents 29
Common Reduction Reactions and Reducing Agents 35
Part II Problems Nucleophiles, Electrophiles, and Redox 41
PART III Synthesis of Monofunctional Target Molecules (1-FG TMs) 45
CHAPTER 3.1 Synthesis of Alcohols (ROH) 47
Synthesis of Alcohols by Functional Group Interconversion (FGI) 48
Synthesis of Alcohols by the Grignard Reaction 50
Synthesis of Propargylic Alcohols (RC=CCH2OH) 56
Synthesis of Phenol Derivatives (ArOH) 57
Example: Alcohol TM 58
CHAPTER 3.2 Synthesis of Alkyl (RX) and Aryl Halides (ArX) 61
Synthesis of Alkyl Halides via Free-Radical Halogenation 61
Synthesis of Alkyl Halides via FGI 62
Retrosynthesis of Alkyl Halides 63
Synthesis of Aryl Halides (ArX) 63
Example: Alkyl Halide TM 64
CHAPTER 3.3 Synthesis of Ethers (ROR') 67
Williamson Ether Synthesis (RX + R'O- ? ROR') 67
Alternate Ether Preparations 68
Synthesis of Epoxides 69
Retrosynthesis of Ethers 70
Example: Ether TM 71
CHAPTER 3.4 Synthesis of Thiols (RSH) and Thioethers (RSR') 73
Example: Thioether TM 75
CHAPTER 3.5 Synthesis of Amines (RNH2) and Anilines (ArNH2) 77
Synthetic Equivalents of NH3 (RX ? RNH2) 78
Synthesis of Amines via Reduction Reactions 80
Retrosynthesis of Amines 82
Synthesis of Aniline Derivatives (ArNH2) 82
Example: Amine TM 83
CHAPTER 3.6 Synthesis of Alkenes (R2C=CR2) 85
Synthesis of Alkenes via FGI 85
Synthesis of Alkenes via the Wittig Reaction 88
Example: Alkene TM 90
CHAPTER 3.7 Synthesis of Alkynes (RC=CR') 93
Synthesis of Alkynes via FGI 93
Synthesis of Alkynes from Other Alkynes (RC=CH ? RC=CR') 94
Example 1: Alkyne TM 95
Example 2: Alkyne TM 95
CHAPTER 3.8 Synthesis of Alkanes (RH) 97
Synthesis of Alkanes via FGI 97
Synthesis of Alkanes via C-C Bond Formation 99
Retrosynthesis of Alkanes 101
Example: Alkane TM 102
CHAPTER 3.9 Synthesis of Aldehydes and Ketones (RCHO, R2C=O) 105
Synthesis of Aldehydes/Ketones via FGI 105
Synthesis of Aldehydes/Ketones via Acyl Substitutions 107
Synthesis of Ketones via a-Alkylation 109
Example: Ketone TM 113
CHAPTER 3.10 Synthesis of Carboxylic Acids (RCO2H) 115
Synthesis of Carboxylic Acids via FGI 115
Synthesis of Carboxylic Acids via Grignard (RMgBr + CO2 ? RCO2H) 116
Carboxylic Acids via a-Alkylation: Malonic Ester Synthesis 117
Example: Carboxylic Acid TM 119
CHAPTER 3.11 Synthesis of Carboxylic Acid Derivatives 121
Relative Reactivities of Carboxylic Acid Derivatives (RCOLG) 121
Synthesis of Acid Chlorides (RCOCl) 123
Synthesis of Anhydrides (RCO2COR) 124
Synthesis of Esters (RCO2R) 124
Synthesis of Amides (RCONH2) 128
Synthesis of Nitriles (RC=N) 131
Example: Carboxylic Acid Derivative 132
Part III Problems Monofunctional Target Molecules (1-FG TMs) 135
PART IV Synthesis of Target Molecules with Two Functional Groups (2-FG TMs) 139
CHAPTER 4.1 Synthesis of ß-Hydroxy Carbonyls and a,ß-Unsaturated Carbonyls 141
The Aldol Reaction 141
Synthesis of a,ß-Unsaturated Esters Using the Wittig Reaction 149
Example: a,ß-Unsaturated Carbonyl 150
CHAPTER 4.2 More Enolate Reactions: Synthesis of 1,3-Dicarbonyls, 1,5-Dicarbonyls, and Cyclohexenones 153
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