Free download Pericyclic Reactions and Organic Photochemistry By Vinay P. Sharma

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Authors of:  Pericyclic Reactions and Organic Photochemistry By Vinay P. Sharma

Vinay P. Sharma

Table of Contents in Pericyclic Reactions and Organic Photochemistry By Vinay P. Sharma

1. INTRODUCTION  

1.1 General Introduction  

1.2 Singlet and Triplet States  

1.3 Classification  

1.3.1 Electrocyclic Reactions  

1.3.2 Cycloadditions  

1.3.3 Sigmatropic Rearrangements  

IFII MOLECULAR ORBITAl, ORBITAL SYMMETRY AND FRONTIER

MOLECULAR ORBITALS  

2.1 Molecular orbital  

2.2 Molecular Orbital Symmetry  

2.3 Frontier Molecular Orbitals (FMO)  

[III PREDICTIONS ABOUT FEASIBILITIES OF PERICYCLIC REACTIONS  

3.1 Woodward-Hoffmann Correlation-diagram Approach  

3.1.1 Precautions in the construction of Correlations Diagrams  

3.2 Frontier Molecular Orbital (FMO) Approach  

3.3 Perturbational Molecular Orbital (PMO) Approach  

1111 ElECTROCYClIC REACTIONS   

4.1 Predictions of Feasibility  

4.1.1 Correlation Diagram Method  

4.1.2 Frontier Molecular Orbital (FMO) Method  

4.1.3 Stereochemical Outcome of Electrocyclic Reactions  

4.1.4 Perturbational Molecular Orbital (PMO) Method  

1111 CYCLOADDITION REACTIONS  

5.1 Suprafacial and Antarafacial Process  

5.2 Correlation Diagram Method  

5.2.1 Diels-Alder Reaction  

5.2.2 Cycloadditions of Benzene and its Derivatives  

5.2.2.1 Reactions between Benzene and Alkenes  

5.2.2.2 Reactions between Benzene and 1,3-butadiene  

5.3 Frontier Molecular Orbital (FMO) Method  

5.4 Perturbational Molecular Orbital (PMO) Method  

5.5 Mechanism of Cycloaddition Reactions  

5.5.1 2 + 2 Cycloadditions  

5.5.2 4 + 2 Cycloadditions  

5.6 2 + 2 Thermal Cycloaddition of Ketenes  

5.7 1,3-Dipolar Cycloadditions  

5.8 Cheletropic Reactions  

1111 SIGMATROPIC REARRANGEMENT  

6.1 Correlation Diagram Method  

6.2 Frontier Molecular Orbital Method  

6.3 Peripatetic Cyclopropane Bridge  

6.4 1,3-Sigmatropic Shift  

6.5 Perturbational Molecular Orbital Method  

6.6 Important Facts about Sigmatropic Rearrangements  

6.7 Some Important Examples of Sigmatropic Rearrangement  

6.7.1 The Cope Rearrangement  

6.7.2 The Claisen Rearrangement  

6.7.3 The Ene Reaction  

6.7.4 Fluxional Tautomerism  

6.7.5 Conversion of Triene to Toluene  

6.7.6 Vinylcyclopropane ~ Cyclopentene Conversion  

6.7.7 1,5-Shift in 1,3-pentadiene  

6.7,8 Precalciferol ~ Calciferol Conversion  

6.7.9 [1,5]-Thermal and [1,7]-photochemical sigmatropic hydrogen

shifts in the isomers of 1,4~di (cycloheptatrienyl) benzene  

6.8 Sequential Sigmatropic Shifts  

6.9 Sigmatropic Migration of Carbon  

lal MISCElLANEOUS  

7.1 Group Transfers and Eliminations  

7.1.1 Group Transfer  

7.1.2 Group-elimination  

7.2 Pericyclic Reactions Involving Ionic Transition States  

7.2.1 Electrocyclic Reactions  

7.2.1.1 FMO Method  

7.2.1.2 PMO Method  

7.2.2 Cycloadditions  

7.2.2.1 PMO Method  

7.2.3 Sigmatropic Reactions  

7.2.3.1 FMO Method  

7.2.3.2 PMO Method  

7.3 Electrocyclic and Sigmatropic Reactions as Cycloadditions  

7.3.1 Electrocyclic Reactions  

7.3.2 Sigmatropic Reactions  

7.4 Woodward-Hoffmann’s Generalized Rules for

Peri cyclic Reactions  

7.5 Secondary Effects  

7.6 2 + 2-Cycloadditions in the Photochemistry of the

cyclohexadienones and Cyclohexenones  

7.7 Aza-Cope Rearrangement  

1111 PROBLEMS AND SOLUTIONS  

8.1 Electrocyclic Reactions  

8.2 Cycloaddition Reactions  

8.3 Sigma tropic Rearrangements  

8.4 Miscellaneous Problems  

8.5 Synthetic Applications of Pericyclic Reactions  

ORGANIC PHOTOCHEMISTRY  

INTRODUOION  

1.1 Activation Energy 189

1.2 Energy Intake (Thermal or Photochemical)  

1.3 Brief History of Photochemistry  

If II BASIC PRINCIPLES  

2.1 Interaction of Electromagnetic Radiation with Matter  

2.2 Laws of Photochemistry  

2.3 Fate of Excited Molecule  

2.4 1Ypes of Excitations  

2.5 Transfer of Excitation Energy: [Sensitisation and Quenching]  

2.6 Quantum YieldiQuantum Efficiency  

2.7 Actinometry  

1111 DETERMINATION OF REACTION MECHANISM  

3.1 Classification: [Thermodynamic Pathways]  

3.2 Rate Constants and Their Relation with the Life-Time of

Reactive Excited States  

3.3 Determination of Rate Constants of Photochemical Reaction  

3.4 Effect of Light Intensity on the Rate of Photochemical Reactions  

3.5 1Ypes of Photochemcial Reactions  

3.6 Photodissociation  

3.7 Gas Phase Photolysis  

IIII ELECTROCYCUC REACTIONS  

4.1 Geometrical Isomerisation  

4.2 Cyclisation Reactions: Valence Isomerisation  

4.3 Photochemical Rearrangements of Alkenes  

4.4 Rearrangement of 1,4-Diene (Di-1t-Methane) Rearrangement  

4.5 Rearrangement of 1,5-Diene  

IIII PHOTOCHEMISTRY OF AROMATIC COMPOUNDS  

5.1 Photochemical Isomerisation of Aromatic Compounds  

5.2 Photochemical addition Reactions Shown by Aromatic Compounds  

5.3 Photochemical Substitution on Aromatic Compounds  

IIII PHOTOCHEMISTRY OF CARBONYL (OMPOUNDS  

6.1 Saturated Acyclic Carbonyl Compounds  

6.2 Norrish Type I (a-Cleavage) Reaction  

6.3 Norrish TYpe II Reactions  

6.4 Photoreduction  

6.5 Saturated Cyclic Carbonyl Compounds  

6.6 ~, y-Unsaturated Carbonyl Compounds  

6.7 a, ~-Unsaturated Carbonyl Compounds  

6.8 Cyclohexadienone  

6.9 Intermolecular Cycloaddition Reactions  

6.10 Photodimerisation of Carbonyl Compounds  

6.11 Oxextane Formation  

1111 MISCELLANEOUS PHOTOCHEMICAL REACTIONS  

7.1 Photo-Fries Rearrangement  

7.2 Photo-Fries Reaction of Anilides  

7.3 Barton Reaction  

7.4 Singlet Molecular Oxygen Reaction  

7.5 Photochemical Formation of Smog  

7.6 Photochemical Degradation of Polymers  

7.7 Photochemistry of Vision  

IIII PROBLEMS AND SOLUTIONS  

8.1 Introduction  

8.2 Basic Principles  

8.3 Determination of Reaction Mechanism  

8.4 Photochemistry of Alkenes  

8.5 Photochemistry of Aromatic Compounds  

8.6 Photochemistry of Carbonyl Compounds  

8.7 Miscellaneous Photochemical Reactions  

APPENDIX  

INDEX  

LOG TABLES

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