ORGANO MAIN GROUP CHEMISTRY -- CONTENTS -- Preface -- 1 Main Group Elements and Heteroatoms: Scope and Characteristics -- 1.1 Aufbau Principle and Sign of Orbitals -- 1.2 Electronic Configuration of an Atom: Main Group Elements and Heteroatoms -- 1.3 Fundamental Properties of Main Group Elements -- 1.4 Acidity of Carboxylic Acid and Substituent Effect -- 1.5 Heteroatom Effect -- 1.5.1 Stabilization of α-Carbocation by Resonance: Stereoelectronic Effect -- 1.5.2 Coordination with Lewis Acids -- References -- Notes 1: Electronegativity -- Notes 2: Importance of Formal Logic-I: Oxidation Number and Formal Charge -- Notes 3: Importance of Formal Logic-II: Octet Rule, Eighteen-Electron Rule, Hypervalence -- 2 Main Group Element Effect -- 2.1 What Is Main Group Element Effect? -- 2.2 Single Bond Energy and π -Bond Energy -- 2.3 Hypervalent Compound -- 2.4 Effect of Hypervalent Bond (1): 3c.4e Bond and Structure -- 2.5 Effect of Hypervalent Bond (2): Apicophilicity and Pseudorotation -- 2.6 Effect of Hypervalent Bond (3): Ligand Coupling Reaction (LCR) and Edge Inversion -- 2.7 Effect of σX-C -- 2.8 Effect of σ.X -C -- Notes 4: (σ, σ*) and (π, π*): HMO (Hueckel Molecular Orbital) and Electrocyclic Reaction -- 3 Lithium, Magnesium, and Copper Compounds -- 3.1 Synthesis -- 3.2 Structure -- 3.3 Reaction -- 3.3.1 Deprotonation as Base -- 3.3.2 Nucleophilic Reaction -- 3.3.3 Conjugate Addition of Lithium Dimethylcuprate -- References -- 4 Boron and Aluminum Compounds -- 4.1 Synthesis -- 4.2 Structure -- 4.3 Reaction -- References -- 5 Silicon, Tin, and Lead Compounds -- 5.1 Synthesis -- 5.2 Reaction -- 5.3 Organotin and Lead Compounds -- References -- Notes 5: Stable Carbene and Its Complex -- 6 Phosphorus, Antimony, and Bismuth Compounds -- 6.1 Phosphorus Compounds -- 6.2 Synthesis of Organophosphorus Compounds.

6.3 Tertiary Phosphine and Its Nucleophilic Reaction -- 6.4 Arbuzov Reaction -- 6.5 Perkow Reaction -- 6.6 Synthesis of Optically Active Phosphines -- 6.7 Ylide and Wittig Reaction and Related Ones -- 6.8 Reactions of Phosphonium Salts and Formation of Phosphoranes -- 6.9 Freezing BPR and Its Effect -- 6.10 Antimony and Bismuth Compounds -- References -- Notes 6: Dreams of Staudinger and Wittig -- Notes 7: Stereochemistry in Nucleophilic Substitution of MX4-type Compounds: Inversion or Retention -- 7 Sulfur, Selenium, and Tellurium Compounds -- 7.1 Sulfur Compounds -- 7.2 Synthesis of Organosulfur Compounds -- 7.3 Reactions of Organosulfur Compounds -- 7.4 Structure and Reaction of Hypervalent Organosulfur Compounds -- 7.5 Selenium and Tellurium Compounds -- References -- Notes 8: Inversion Mechanism of NH3 and NF3: Vertex Inversion or Edge Inversion -- 8 Organohalogen Compounds: Fluorine and Iodine Compounds -- 8.1 Synthesis of Chlorine and Bromine Compounds -- 8.2 Fluorine Compounds -- 8.3 Iodine Compounds -- References -- 9 Atrane and Transannular Interaction: Formation of Hypervalent Bond -- 9.1 Introduction -- 9.2 Silatrane and Atrane -- 9.3 Transannular Interaction (1) -- 9.4 Transannular Interaction (2) -- References -- 10 Unsaturated Compounds of Main Group Elements of Third Period and Heavier -- 10.1 Introduction -- 10.2 Unsaturated Bonds of Group 15 Elements of Third Period and Heavier -- 10.3 Unsaturated Bonds of Group 14 Elements of Third Period and Heavier -- 10.4 Aromatic Compounds of Group 14 Elements -- References -- 11 Ligand Coupling Reaction -- 11.1 Introduction -- 11.2 Selectivity of Ligand Coupling Reaction: Theoretical Investigation -- 11.3 Ligand Coupling Reaction of Organic Compounds of Phosphorus, Antimony, and Bismuth -- 11.4 Ligand Coupling Reaction of Organic Compounds of Sulfur, Selenium, and Tellurium.

11.5 Ligand Coupling Reaction of Organoiodine Compounds -- References -- Notes 9: Hexavalent Organotellurium Compounds -- 12 Hypervalent Carbon Compounds: Can Hexavalent Carbon Exist? -- 12.1 Introduction -- 12.2 Attempts for Pentacoordinate Hypervalent Carbon Species -- 12.3 Synthesis of Pentacoordinate Hypervalent Carbon Species (10-C-5) and Bond Switching at Carbon and Boron -- 12.4 Attempts to Hexacoordinate Hypervalent Carbon Species (12-C-6) -- References -- Notes 10: Main Group Element Porphyrins -- Index.