ROBOTICS & AUTOMATION
Empowering Progress
Up to 25% off Essentials Robotics and Automation titles
Stereochemistry and Organic Reactions
Conformation, Configuration, Stereoelectronic Effects and Asymmetric Synthesis
- 1st Edition - April 21, 2021
- Author: Dipak Kumar Mandal
- Language: English
- Paperback ISBN:9 7 8 - 0 - 1 2 - 8 2 4 0 9 2 - 2
- eBook ISBN:9 7 8 - 0 - 1 2 - 8 2 4 0 9 3 - 9
Stereochemistry and Organic Reactions: Conformation, Configuration, Stereoelectronic Effects and Asymmetric Synthesis provides coverage on the stereochemistry of reactions… Read more
Purchase options
Institutional subscription on ScienceDirect
Request a sales quoteStereochemistry and Organic Reactions: Conformation, Configuration, Stereoelectronic Effects and Asymmetric Synthesis provides coverage on the stereochemistry of reactions of all mechanistic types, ranging from ionic, pericyclic and transition metal-catalyzed to radical and photochemical. Chapters cover acyclic molecules, cyclic molecules, the stereochemistry of organic reactions, the perturbation molecular orbital theory for the origin of stereoelectronic effects, and an introduction to the principles of stereoselectivity and hierarchical levels of asymmetric synthesis. Each chapter includes problems that reinforce main themes, making it valuable to students, teachers and researchers working in organic, biological and medicinal chemistry, as well as biologists, pharmacologists, polymer chemists and chemists.
- Presents a holistic and unified approach to stereochemical understanding and predictions, covering reactions of all mechanistic classes
- Includes two background chapters on perturbation theory and stereoselective principles, along with asymmetric designs
- Features novel rules and mnemonics to delineate product stereochemistry
- Includes up-to-date coverage with over 1300 selective references
Organic chemistry students, including advanced undergraduates and graduate students. Organic chemists working in academia and industry needing foundational information on topics covered
- Cover image
- Title page
- Table of Contents
- Copyright
- Preface
- Abbreviations
- Part I: Stereochemistry of organic molecules
- Introduction
- Chapter 1: Acyclic molecules 1: Conformation and symmetry
- Abstract
- 1.1: Stereoisomerism in molecules
- 1.2: Representation of tetrahedral molecules: Perspective (flying wedge, zigzag) and projection (Fischer, sawhorse, Newman) formulas
- 1.3: Conformation
- 1.4: Symmetry in molecules53,54
- 1.5: Symmetry point groups
- Chapter 2: Acyclic molecules 2: Configuration and resolution
- Abstract
- 2.1: Distinction between configuration and conformation
- 2.2: Classification of isomerism
- 2.3: Stereogenic centre, chiral centre, chiral molecule and enantiomers
- 2.4: Chirality and optical activity
- 2.5: Chiral centres other than carbon15,16
- 2.6: Stereocentre configuration
- 2.7: Absolute configuration and descriptors
- 2.8: Relative configuration and descriptors
- 2.9: Stereogenic axis
- 2.10: Planar chirality
- 2.11: Molecules that are inherently chiral
- 2.12: Topicity of ligands and faces
- 2.13: Resolution
- 2.14: Determination of enantiomeric composition
- Chapter 3: Cyclic molecules: Configuration and conformation
- Abstract
- 3.1: Configuration of cyclic molecules
- 3.2: Cyclic conformation: Introduction and Baeyer strain theory
- 3.3: Conformation of cyclohexane
- 3.4: Conformation of monosubstituted cyclohexanes: Conformational free energy (or A Value)
- 3.5: Conformation of disubstituted cyclohexanes
- 3.6: Conformation of polysubstituted cyclohexanes
- 3.7: Conformation of six-membered saturated heterocycles61,62
- 3.8: The anomeric effect69–71
- 3.9: Conformation of cyclohexyl systems with a double bond
- 3.10: Monocyclic systems other than cyclohexane
- 3.11: Fused ring systems
- 3.12: Determination of configuration and conformation using chiroptical methods151,152
- Part II: Introduction to stereoelectronic effects and stereoselective reactions
- Introduction
- Chapter 4: Perturbation theory and organic reactions
- Abstract
- 4.1: Molecular orbitals (MOs)
- 4.2: Perturbation theory
- 4.3: Ionic reactions10
- 4.4: Pericyclic reactions22,23
- 4.5: Radical reactions39,40
- 4.6: Photochemical reactions48
- Chapter 5: Introduction to stereospecificity, stereoselectivity and asymmetric synthesis
- Abstract
- 5.1: Conformation and reactivity1
- 5.2: Stereospecific and stereoselective reactions7,8
- 5.3: Asymmetric synthesis10–12
- Part III: Stereochemistry of organic reactions
- Introduction
- Chapter 6: Ionic reactions 1: Fundamental stereochemistry
- Abstract
- 6.1: Substitution reactions
- 6.2: Elimination reactions
- 6.3: Fragmentation reactions
- 6.4: Addition reactions of alkenes and alkynes
- 6.5: Nucleophilic addition to cyclohexanones
- 6.6: Iodolactonization
- Chapter 7: Ionic reactions 2: Diastereoselectivity and asymmetric synthesis
- Abstract
- 7.1: Diastereoselective carbonyl additions: Chiral substrates with α-stereocentres
- 7.2: Diastereoselective carbonyl additions: Chiral substrates with β-stereocentres
- 7.3: Asymmetric carbonyl reductions: Chiral reagents
- 7.4: Asymmetric deprotonations: Chiral bases
- 7.5: Asymmetric carbonyl additions/reductions: Chiral catalysts
- 7.6: Diastereoselective enolate formation
- 7.7: Asymmetric enolate alkylations
- 7.8: Diastereoselective aldol reactions
- 7.9: Asymmetric aldol reactions
- 7.10: Asymmetric allylation reactions
- 7.11: Asymmetric synthesis of amines
- 7.12: Diastereoselective addition to alkenes
- 7.13: Asymmetric addition to alkenes
- 7.14: Asymmetric conjugate additions
- 7.15: Enzyme-catalysed asymmetric reactions
- Chapter 8: Pericyclic reactions 1: Basic stereochemistry
- Abstract
- 8.1: The Diels–Alder reaction
- 8.2: 1,3-Dipolar cycloaddition reactions15–18
- 8.3: Ketene cycloadditions26,27
- 8.4: The Wittig reaction
- 8.5: Carbene cycloadditions39–42
- 8.6: The ene reaction51–53
- 8.7: Retro-ene reactions: Pyrolytic syn eliminations
- 8.8: Thermal electrocyclic reactions71
- 8.9: Rearrangement reactions: [1,2] sigmatropic shifts
- 8.10: [1,3], [1,5] and [1,7] sigmatropic rearrangements
- 8.11: The Cope rearrangement94,95
- 8.12: The Claisen rearrangement104–106
- 8.13: The Wittig rearrangement119,120
- Chapter 9: Pericyclic reactions 2: Asymmetric synthesis
- Abstract
- 9.1: Asymmetric Diels–Alder reactions1–5
- 9.2: Asymmetric 1,3-dipolar cycloaddition reactions30
- 9.3: Asymmetric cyclopropanation reactions42–45
- 9.4: Asymmetric ene reactions66, 67
- 9.5: Asymmetric Claisen rearrangements80–83
- 9.6: Asymmetric Wittig and related rearrangements96–100
- Chapter 10: Transition metal-catalysed reactions: Diastereoselectivity and asymmetric synthesis
- Abstract
- 10.1: Diastereoselective epoxidation
- 10.2: Asymmetric epoxidation
- 10.3: Asymmetric dihydroxylation and aminohydroxylation
- 10.4: Asymmetric hydrogenation51,52
- 10.5: Asymmetric palladium-catalysed coupling reactions
- Chapter 11: Radical reactions: Stereochemistry and asymmetric synthesis
- Abstract
- 11.1: Radical chain mechanisms
- 11.2: Diastereoselective intermolecular radical reactions10
- 11.3: Diastereoselective radical cyclization reactions31, 32
- 11.4: Dissolving metal reductions
- 11.5: Asymmetric radical reactions
- Chapter 12: Photochemical reactions: Stereochemistry and asymmetric synthesis
- Abstract
- 12.1: Photochemical [2 + 2] cycloadditions1–4
- 12.2: Stereochemistry of photochemical electrocyclic reactions
- 12.3: Stereochemistry of photo-induced remote functionalization
- 12.4: Stereochemistry of photochemical rearrangements
- 12.5: Asymmetric photochemical reactions67, 68
- Appendix: Answers to problems
- Abstract
- Index
- No. of pages: 638
- Language: English
- Edition: 1
- Published: April 21, 2021
- Imprint: Academic Press
- Paperback ISBN: 9780128240922
- eBook ISBN: 9780128240939
DM
Dipak Kumar Mandal
Dipak K. Mandal is a former professor of chemistry at Presidency College/University, Kolkata, India. He completed his doctoral thesis under the supervision of Professor N. K. Sinha at the Bose Institute, Kolkata and carried out postdoctoral work in the USA from 1990-1993 with Professor C. Fred Brewer at Albert Einstein College of Medicine, New York. He has been involved in teaching undergraduate and graduate level organic chemistry for about 35 years and is the author of the books titled Pericyclic Chemistry (Elsevier, 2018) and Stereochemistry and Organic Reactions (Academic Press, 2021). His keen interest in chemical education resulted in three publications in the Journal of Chemical Education. His research interests include protein folding, structure and dynamics, and peptide synthesis. He was actively engaged in guiding research and published many research papers in peer-reviewed international journals.
Affiliations and expertise
Formerly of Presidency College/University, Kolkata, IndiaRead Stereochemistry and Organic Reactions on ScienceDirect