Organic sulfur chemistry

SULFUR BONDING. INTRODUCTION. PROPERTIES OF SULFUR BONDS. PARTICIPATION OF 3D ORBITALS IN SULFUR BONDING. BONDING IN TRI- AND TETRACOORDINATE SULFUR. WHY ARE a-DISULFOXIDESSO UNSTABLE? s-SULFURANE-HYPERVALENCY. HYPERVALENT INTERACTIONS. THE STEREOELECTRONIC EFFECTS OF SULFUR GROUPS. INTRODUCTION. DICOORDINATE SULFUR GROUPS. Electron-Releasing Conjugative Effects. Electron-Sharing Conjugative Effects. Electron-Accepting Conjugative Effects. TRICOORDINATE AND TETRACOORDINATE SULFUR GROUPS. NEIGHBORING GROUP EFFECTS OF SULFUR GROUPS. Dicoordinate Sulfur Groups. Sulfoxides. STEREOCHEMISTRY. INTRODUCTION. TRICOORDINATE SULFUR COMPOUNDS. Structure and Pyramidal Inversion. Sulfoxides. Sulfinate and Thiosulfinate Esters. Sulfonium and Alkoxysulfonium Salts. Sulfilimine and Related Derivatives. Other Tricoordinate Sulfur Compounds. TETRACOORDINATE SULFUR COMPOUNDS. PENTACOORDINATE AND POLYCOORDINATE SULFUR COMPOUNDS. STEREOCHEMISTRY OF a-SULFINYL CARBANIONS. STEREOCHEMISTRY OF a-SULFONYL CARBANIONS. SUBSTITUTION. INTRODUCTION. DICOORDINATE SULFUR COMPOUNDS. Nucleophilic Substitution. Free Radical Substitution. TRICOORDINATE SULFUR COMPOUNDS. Nucleophilic Substitution by SN1-Type Reactions. Nucleophilic Substitution by Ligand Exchange. NUCLEOPHILIC SUBSTITUTIONS ON TETRACOORDINATE SULFUR ATOM-POSSIBLE INVOLVEMENT OF HYPERVALENT INTERMEDIATES. Mode of Bond Fission and Electronic Effects. Effect of Ring Size. Neighboring Group Participation. Reactions at the a-Carbon. PENTACOORDINATE SULFUR COMPOUNDS. LIGAND COUPLING REACTIONS WITHIN HYPERVALENT SPECIES. CONCEPT OF LIGAND COUPLING WITHIN s-SULFURANE INTERMEDIATES. STEREOCHEMISTRY OF LIGAND COUPLING ON SULFUR. LIGAND COUPLING AND LIGAND EXCHANGE ON SULFUR. LIGAND COUPLING AND PSEUDOROTATION. OTHER EXAMPLES. LIGAND COUPLING ON OTHER ATOMS. OXIDATION OF SULFOXIDES WITH METAL OXIDES. REDUCTION OF SULFILIMINES WITH METAL HYDRIDES. OXIDATION AND OXYGENATION. INTRODUCTION. OXIDATION OF THIOLS TO DISULFIDES. Air Oxidation . Metal Oxides and Metallic Ions. Sulfoxides, Amine N-Oxides and Peroxides. Halogens and Halogenating Agents. Nitrogen Compounds. Flavin Derivatives. Photo-Oxidation. OXIDATION OF THIOLS AND DISULFIDES TO SULFUR SPECIES OF HIGHER OXIDATION STATES. Nucleophilic Oxidation. Electrophilic Oxidation. Oxygenation with Enzymes. OXIDATION AND OXYGENATION OF SULFIDES AND SULFOXIDES. Electrophilic Oxidation. Nucelophilic Oxidation. One-Electron Transfer Oxygenation-A Comparison of Cytochrome P-450 and FAD-Containing Monooxygenase. Stereochemistry. REDUCTION. INTRODUCTION. REDUCTION OF DISULFIDES TO THIOLS. Metal Hydrides. Electron Transfer and Photolysis. Thiols and Selenols. Formamidinesulfinic Acid. Tricoordinate Phosphorus Compounds. REDUCTION OF SULFENIC ACID AND SULFENIC ACID DERIVATIVES. Thiols. Electrode Reduction. Silicon and Tin Hydrides. REDUCTION OF SULFINIC ACID AND SULFINIC ACID DERIVATIVES. Phosphorus Compounds. Hydrogen Halides and Trimethylsilyl Iodide. Lithium Aluminum Hy dride. Hydrazine. T