Organic synthesis : concepts and methods
"Since it is one of the core disciplines, every student of organic chemistry will need to cover organic synthesis at some point. This third edition of an extremely well-received and proven textbook is specially written with advanced undergraduate and graduate students in mind, although it is equally useful for research chemists, too. The text has been enlarged by 15% to include new chapters on combinatoric chemistry, non-covalent molecular assemblies and the use of the internet for searching chemical compounds. The authors have chosen the methods included here for their efficiency, elegance, and didactic value and have highlighted important reactions within the text. Book jacket."--BOOK JACKET
Print Book,English, 2003
3rd, completely rev. and enl. edView all formats and editions
Wiley-VCH, Weinheim, 2003
xvi, 517 pages : illustrations ; 25 cm
9783527302727, 9783527302734, 9781560818236, 3527302727, 3527302735, 1560818239
51068223
1. Synthesis of carbon chains
1.1. Introduction
1.2. Functional group arrangements
1.3. Umpolung
1.4. Alcohols
1.5. Synthesis of alkenes and their coupling reactions
1.6. Aldehydes, ketones, and carboxylic acids
1.7. 1,2-difunctional compounds
1.8. 1,3-difunctional compounds
1.9. 1,4-difunctional compounds
1.10. 1,5-difunctional compounds
1.11. 1,6-difunctional compounds
2. Carbocycles
2.1. Introduction
2.2. Radicals
2.3. Ring closing metathesis
2.4. Macrocyclization
2.5. Cyclopropane and cyclopropene derivatives
2.6. Cyclobutane derivatives
2.7. Cyclopentane derivatives
2.7.1. Prostaglandins
2.8. Cyclohexane and cyclohexene derivatives
2.8.1. Steroids
2.9. Bridged carbocycles. 3. Functional group interconversion (FGI)
3.1. Introduction
3.2. Reduction
3.2.1. General considerations
3.2.2. Hydrogenation of carbon-carbon multiple bonds and cyclopropane rings
3.2.3. Reduction of aldehydes, ketones, and carboxylic acid derivatives
3.2.4. Reduction of nitrogen compounds
3.2.5. Reductive cleavage of carbon-heteroatom and heteroatom-oxygen bonds
3.3. Oxidation
3.3.1. General considerations
3.3.2. Oxidation of non-functional carbon atoms
3.3.3. Oxidation of carbon atoms in carbon-carbon multiple bonds
3.3.4. Oxidation of alcohols to aldehydes, ketones, and carbonxylic acids
3.3.5. Oxidative rearrangement and cleavage of ketones and aldehydes
3.3.6. Olefin syntheses by dehydrogenation and other elimination reactions
3.4. Synthesis of carboxylic acid derivatives
3.5. Ethers
3.6. Phosphonates
3.7. Sulfides and sulfonates
3.8. Halides
3.9. Protection of functional groups
3.9.1. Reaction carbon-hydrogen and carbon-carbon bonds
3.9.2. Alcoholic hydroxyl groups
3.9.3. Amino groups and thiols
3.9.4. Carboxyl groups
3.9.5. Aldehyde and keto groups
3.9.6. Phosphate groups. 4. Heterocycles and arenes
4.1. Introduction
4.2. Nitrogen-containing heterocycles and arenes in drugs
4.3. Lactones (oxetanones) and lactams (azetidinones)
4.4. Porphyrins, chlorophyll a, and corrins
4.5. Alkaloids
4.6. Self-reproduction of chirality
4.7. Monosaccharides and protected derivatives
5. Biopolymers and dendrimers
5.1. Introduction
5.2. Oligonucleotides
5.3. Peptides
5.3.1. Stages of peptide synthesis
5.4. Di- and oligosaccharide syntheses
5.5. Dendrimers
6. Combinatorial mixtures and selection
6.1. Introduction
6.2. The split method and multicomponent reactions
6.3. Coding
6.4. Libraries for different purposes
6.4.1. Ligands for metal ions
6.4.2. Catalysts
6.4.3. Proteins
6.4.4. Nucleic acids
6.4.5. Heterocycles
6.4.6. Carbocycles
6.4.7. Chiral compounds. 7. Concepts in nanometer-sized skeletons and modules
7.1. Introduction
7.2. Nucleic acids
7.2.1. DNA with a site-specifically, covalently bound mutagen
7.2.2. Cationic oligonucleotides
7.2.3. A synthetic scissor for sequence-specific DNA cleavage
7.2.4. Hexose oligonucleotides
7.2.5. DNA helicates with a central copper(I) ion wire
7.3. Kemp's acid : enzyme-cleft and self-replication models
7.3.1. Enzyme-cleft models with convergent functional groups
7.3.2. A synthetic self-replicating system
7.4. Covalent and non-covalent porphyrin assemblies
7.5. Molecular assemblies of amphiphiles
7.5.1. Vesicle membranes
7.5.2. Helical micellar fibers
7.6. Capsules
7.7. Fullerenes and carbon rods
7.8. Rotaxanes and catenanes
8. The Internet and the feedstock
8.1. Introduction
8.2. Starting materials
8.3. Literature search
8.3.1. Science finder scholar (Chemical Abstract Service, CAS)
8.3.2. American Chemical Society (ACS)
8.3.3. European journals
8.3.4. Organic chemistry handbooks
8.4. Feedstock. 9. Retrosynthetic analysis, sketches of syntheses, tandem reactions and green chemistry
9.1. Introduction
9.2. Elementary retrosynthetic analysis
9.2.1. Open-chain compounds
9.2.2. Mono- and bicyclic target molecules
9.2.3. Bridged polycyclic molecules
9.2.4. Summary of antithetical analysis of simple molecules
9.3. Learning from research papers
9.4. Tandem reactions
9.5. Green chemistry
10. Seventy-seven conclusions in alphabetical order
10.1. Introduction
10.2. Conclusions in alphabetical order
11. References
Previous ed. published as: Organic synthesis: concepts, methods, starting materials. Weinheim : Wiley-VCH, 1994