Photochemistry and Pericyclic Reactions (3rd Edition)

This complete new and innovative textbook provides a comprehensive account of pericyclic reactions and organic photochemistry for undergraduate and postgraduate courses. The approach is based on mechanism and reaction type, and the subject matter is developed and concentrated on its understanding ra...

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Bibliographic Details
Main Authors Singh, Jagdamba, Singh, Jaya
Format eBook
LanguageEnglish
Published Kent New Academic Science 2012
Edition3
Subjects
Chemistry & Chemical Engineering
General References
Organic photochemistry
Pericyclic reactions
Ring formation (Chemistry)
Textbooks
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Cover

Table of Contents:
  • Title Page Prefaces Table of Contents 1. Pericyclic Reactions 2. Electrocyclic Reactions 3. Cycloaddition Reactions 4. Sigmatropic Rearrangement 5. Group Transfer Reactions 6. Introduction and Basic Principles of Photochemistry 7. Photochemistry of Carbonyl Compounds 8. Photo Rearrangements 9. Photo Reduction and Photo Oxidation 10. Photochemistry of Alkenes, Dienes and Aromatic Compounds 11. Photo Substitution Reactions at sp3 Hybrid Carbon Having at Least One Hydrogen 12. Photochemistry in Natural Products 13. Photochemistry in Nature and Applied Photochemistry 14. Problems and Their Solutions Index
  • Further Reading -- Problems -- Chapter-11. Photo Substitution Reactions at sp3 Hybrid Carbon Having at Least One Hydrogen -- 11.1 Introduction -- 11.2 Barton Reaction -- 11.3 The Hoffmann - Loeffler - Freytag Reaction -- 11.4 Photolysis of Hypohalites -- Glossary -- Further Reading -- Problems -- Chapter-12. Photochemistry in Natural Products -- 12.1 Photo Rearrangement or Isomerisation -- 12.2 Photochemistry of Natural Products Containing Bicyclo [3, 1, 0] Hexane - 2 - One Residue -- 12.3 Photochemistry of Natural Products Having β, γ-Unsaturated Ketone Group -- 12.4 Photochemistry of Natural Products Having Epoxy Ketone System -- 12.5 Dye - Sensitised Photooxygenations -- 12.6 Photochemistry of Saturated Ketones -- Chapter-13. Photochemistry in Natur and Applied Photochemistry -- 13.1 Photochemical Reactions in the Atmosphere -- 13.2 Chemistry of Vision -- 13.3 Photography -- 13.4 Light-Absorbing Compounds -- 13.5 Photochromism -- 13.6 Photoimaging -- 13.7 Photochemistry of Polymers -- Problems -- Chapter-14. Problems and Their Solutions -- Index
  • 7.8 [2 + 2] Cycloaddition Reaction of Enones with Alkenes -- Glossary -- Further Reading -- Problems -- Chapter-8. Photo Rearrangements -- 8.1 Photo Rearrangement of Cyclopentenone -- 8.2 Cyclohexanone Rearrangements -- 8.2.1 Lumiketone Rearrangement -- 8.2.2 Di-π Methane Type Rearrangement -- 8.3 Rearrangement of Dienones -- 8.4 Photo Rearrangements of b, y-Unsaturated Ketones -- 8.4.1 Mechanism of 1,2 - Acyl Shift -- 8.4.2 Mechanism of 1,3 - Acyl Shift -- 8.5 Aza - Di - Methane Rearrangement -- 8.6 Di-π-Methane (DPM) Rearrangement -- 8.7 Rearrangements in Aromatic Compounds -- Glossary -- Further Reading -- Problems -- Chapter-9. Photo Reduction and Photo Oxidation -- 9.1 Photo Reduction of Carbonyl Compounds -- 9.2 Photo Reduction of Aromatic Hydrocarbons -- 9.3 Photochemical Oxidations -- 9.4 Photo Oxidation of Alkenes and Polyenes -- Glossary -- Further Reading -- Problems -- Chapter-10. Photochemistry of Alkenes, Dienes and Aromatic Compounds -- 10.1 Photochemistry of Alkenes -- 10.2 Cis-Trans Isomerisation of Alkenes -- 10.2.1 Cis-Trans Isomerisation of Alkenes by Direct Irradiation -- 10.2.2 Sensitised Cis-Trans isomerisation -- 10.3 Dimerisation of Alkenes -- 10.3.1 Intramolecular Dimerisation -- 10.4 Photochemistry of Conjugated Dienes -- 10.4.1 Photochemistry of conjugated Dienes in Solution -- 10.5 Photoisomerisation of Benzene and Substituted Benzene -- 10.5.1 1,2-Alkyl Shift -- 10.5.2 Mechanism of 1, 3-Alkyl Group Shift -- 10.6 Photoaddition of Alkenes to Aromatic Benzenoid compounds -- 10.6.1 1, 2-Cycloaddition Reactions -- 10.6.2 1, 3-Photoaddition of Benzene -- 10.6.3 1, 4-Photoaddition of Benzenes -- 10.7 Addition of Oxygen -- 10.8 Aromatic Photosubstitution -- 10.8.1 Type A Reactions -- 10.8.2 Type B Substitutions -- 10.8.3 Radical Substitutions -- 10.9 Photochemistry of Diazo Compounds -- 10.10 Photochemistry of Azides -- Glossary
  • 4.9 Fluxional Molecules -- Glossary -- Further Reading -- Problems -- Chapter-5. Group Transfer Reactions -- 5.1 Ene Reactions -- 5.2 Group Transfer Reactions Given by Diimide -- Glossary -- Further Reading -- Problems -- Chapter-6. Introduction and Basic Principles of Photochemistry -- 6.1 Energy of a Molecule -- 6.2 Photochemical Energy -- 6.2.1 Photochemical Excitation of the Molecule -- 6.3 Electronic Transitions -- 6.3.1 Types of electronic Excitation and Molecular Orbital View of Excitation -- 6.4 Spin Multiplicity -- 6.5 Nomenclature of Excited States -- 6.6 The Fate of the Excited Molecule - Physical Processes : Jablonski Diagram -- 6.7 Photolytic Cleavage -- 6.8 Laws of Photochemistry -- 6.8.1 Grotthurs - Drapper Law -- 6.8.2 Einstein's Law of Photochemical Equivalence -- 6.9 Quantum Yield or Quantum Efficiency -- 6.9.1 The Reasons for High Quantum Yield -- Further Reading -- Problems -- Chapter-7 Photochemistry of Carbonyl Compounds -- 7.1 α- Cleavage or Norrish type I Process -- 7.1.1 Norrish Type I Process Given by Acyclic Saturated Ketones -- 7.1.2 Norrish Type I Reaction of Saturated Cyclic Ketones -- 7.1.3 Norrish Type I Process Given by Cyclopentanones -- 7.14 a-Cleavage Given by Cyclobutanones -- 7.2 β-Cleavage Reaction -- 7.3 Intramolecular Hydrogen Abstraction (y-Hydrogen Abstraction) -- 7.4 Hydrogen Abstraction From Other Sites -- 7.4.1 B-Hydrogen Abstraction -- 7.4.2 and e-Hydrogen Abstraction -- 7.4.3 Hydrogen Abstraction from Distant Sites -- 7.5 Formation of Photoenols or Photoenolisation -- 7.6 Intermolecular Hydrogen Transfer : Intermolecular Photo Reduction -- 7.7 Photocycloaddition Reaction (Paterno - Buchi Reaction) -- 7.7.1 Addition of Electron - Rich Alkenes -- 7.7.2 Addition to Electron Deficient Alkenes -- 7.7.3 Oxitane Formation with Dienes and Alkynes -- 7.7.4 Intramolecular Paterno - Buchi Reaction
  • 3.2 Theory of Cycloaddition Reactions : FMO Method -- 3.2.1 [2 + 2] Cycloaddition Reactions -- 3.2.2 [4 + 2] Cycloaddition Reactions -- 3.3 Correlation Diagrams of Cycloaddition Reactions -- 3.3.1 Orbital Symmetry in Cycloaddition -- 3.3.2 Correlation Diagram of [4 + 2] Cycloaddition Reaction -- 3.4 The Woodward - Hoffmann Rule for Cycloaddition Reactions -- 3.4.1 The Woodward-Hoffmann Rule in | 4 + 2 | Cycloadditions -- 3.4.2 Woodward-Hoffmann Rule in |2 + 2| Cycloadditions -- 3.5 Huckel - Mobius Method -- 3.6 Cycloreversion or Retrocycloaddition Reactions -- 3.7 [4 + 2 ] Cycloadditions of Cations and Anions -- 3.8 Cycloadditions Involving More Than [4 + 2] Electrons -- 3.9 Some Anomalous [2 + 2] Cycloadditions -- 3.10 Chelotropic Reactions -- 3.10.1 [2 + 2] Chelotropic Cycloadditions -- 3.11 Chelotropic Elimination -- 3.12 1, 3- Dipolar Cycloadditions -- 3.12.1 Stereochemistry of 1, 3-Dipolar Cycloadditions -- Glossary -- Further Reading -- Problems -- Chapter-4. Sigmatropic Rearrangement -- 4.1 Introduction and Classification -- 4.1.1 Classification of Sigmatropic Rearrangements -- 4.1.2 Name of the Rearrangement -- 4.2 Mechanism of Sigmatropic Rearrangement -- 4.2.1 Sigmatropic Shifts of Alkyl Group -- 4.2.2 Selection Rules for Sigmatropic Rearrangement -- 4.3 Other Sigmatropic Shifts -- 4.3.1 Cope Rearrangement -- 4.3.2 Claisen Rearrangement -- 4.4 [2,3] Sigmatropic Rearrangements -- 4.5 Some Other [m,n] Sigmatropic Rearrangements -- 4.6 The Woodward - Hoffmann Rule for Sigmatropic Rearrangement -- 4.6.1 The Woodward - Hoffmann Rule for (m, n] Sigmatropic Rearrangement where Migrating Group is not Hydrogen -- 4.6.2 The Woodward - Hoffmann Rule for (m, n) Sigmatropic Rearrangement where Migrating Group is Hydrogen -- 4.7 Huckel - Mobius Method in Sigmatropic Rearrangements -- 4.8 Modified and Degenerate Cope Rearrangement
  • Cover -- Preface to the Third Edition -- Preface to the First Edition -- Chapter-1. Pericyclic Reactions -- 1.1 Introduction -- 1.2 Construction of π Molecular Orbitals of Ethylene and 1, 3-Butadiene -- 1.3 Symmetry in π Molecular Orbital -- 1.4 Filling of Electrons in π Molecular Orbitals in Conjugated Polyenes -- 1.5 Construction of Molecular Orbitals of Conjugated Ions and Radicals -- 1.6 Frontier Molecular Orbitals -- 1.7 Excited States -- 1.8 Symmetries in Carbon-Carbon Sigma Bond -- 1.9 Theory of Pericyclic Reactions -- Glossary -- Further Reading -- Problems -- Chapter-2. Electrocyclic Reactions -- 2.1 Introduction -- 2.2 Conrotatory and Disrotatory Motions in Ring-Opening Reactions -- 2.3 Conrotatory and Disrotatory Motion in Ring -Closing Reactions -- 2.3.1 Open Chain Conjugated System Having 4n Conjugated Electrons -- 2.3.2 Open Chain Conjugated System Having (4n + 2) π Conjugated Electrons -- 2.4 Frontier Molecular Orbital (FMO) Method -- 2.4.1 Cyclisation of 4n π Systems -- 2.4.2 Electrocyclic Ring - Opening in which Polyene has 4n π Electrons -- 2.4.3 Cyclisation of (4n + 2) Systems -- 2.4.4 Electrocyclic Ring - Opening in which Polyene has (4n + 2) Electrons -- 2.4.5 Selection Rules and Microscopic Reversibility -- 2.5 Correlation Diagram -- 2.5.1 Correlation Diagram of the Electrocyclic Reaction in Which Polyene has 4n Electrons -- 2.5.2 Correlation Diagram of Electrocyclic Reaction in which Polyene has (4n + 2) π Electrons -- 2.6 The Woodward - Hoffmann Rule for Electrocyclic Reactions -- 2.6.1 Woodward - Hoffmann Rule for Electrocyclic Thermal Reactions -- 2.6.2 Photochemical Electrocyclic Reactions -- 2.7 Huckel - Mobius (H-M) Method or Perturbation Molecular Orbital (PMO) Method -- Glossary -- Further Reading -- Problems -- Chapter-3. Cycloaddition Reactions -- 3.1 Introduction