Aromatic Thiols and Their Derivatives

Preface
Introduction
References
Contents
1 Synthesis of Aromatic Thiols
1.1 Reactions of Aromatic Compounds with Elemental Sulfur and its Inorganic Compounds
1.2 Reactions with Other Sulfur-containing Nucleophiles
1.3 Reactions with Sulfur-containing Electrophiles
1.4 Reduction of Diaryl Disulfides
1.5 Examples of Syntheses
1.5.1 Synthesis of 2- and 3-substituted Aryl Thiols from Diazonium Chlorides and Potassium Ethylxanthogenate
1.5.2 Synthesis of 4-substituted Aryl Thiols via Reduction of Aromatic Sulfonyl Chlorides
1.5.3 Synthesis of Aryl Thiols via Reduction of Diaryl Disulfides
References
2 Aromatic Sulfides
2.1 General Approaches to the Synthesis of Aryl Sulfides
2.2 Transition Metal-Catalyzed Methods of the C–S Bond Formation
2.3 Directed Synthesis of Substituted Aromatic Sulfides
2.3.1 Alkyl Aryl Sulfides
2.3.1.1 Alkylation of Aryl Thiols with Primary and Secondary Alkyl Halides
2.3.1.2 Other Methods
2.3.2 tert-Alkyl Aryl Sulfides
2.3.3 Diaryl Sulfides
2.3.4 Vinyl Sulfides
2.3.5 Benzyl Thiols and Benzyl Sulfides
2.3.6 Dialkyl Sulfides
2.4 Examples of Syntheses
2.4.1 Reactions of Thiols with Primary and Secondary Alkyl Halides
2.4.2 Reactions of Thiols with Tertiary Alkyl Halides and Alcohols
2.4.3 Reactions of Thiols with Alkenes
2.4.4 Reactions of Thiols with Acetylenes
2.4.5 Diaryl Sulfides
2.4.6 Functionally Substituted Alkyl Aryl Sulfides
References
3 Aromatic Disulfides, Sulfoxides, Sulfones, and Other Derivatives of Aromatic Thiols
3.1 Aromatic Disulfides
3.2 Aromatic Sulfoxides
3.3 Aromatic Sulfones
3.4 S-Alkyl, S-Aryl, S-Benzylthioacylates, and Organylthiobenzoates
3.5 2-(Arylthio)ethyl acylates
3.6 Dithiocarboxylic Acid Dibenzyl Esters
3.7 Derivatives of Aromatic Selenols
3.8 Examples of Syntheses
3.8.1 Aromatic Sulfoxides
3.8.2 Alkyl Aryl Sulfones
3.8.3 Alkyl-, Aryl- and Benzylthioacylates
3.8.4 Dithiocarboxylic Acid Dibenzyl Esters
3.8.5 Derivatives of Aromatic Selenols
References
4 Reactivity of Aromatic Thiols and Their Derivatives
4.1 Electrochemical Oxidation of Aryl Thiols and Their Derivatives
4.1.1 Aryl Thiols
4.1.1.1 Structural Effects in Electrochemical Oxidation of Substituted Thiophenols
4.1.1.2 Protolytic and Electrochemical Stages in Oxidation of Thiophenols
4.1.2 Aromatic Sulfides
4.1.2.1 Alkyl Phenyl Sulfides
4.1.2.2 Substituted Thioanisoles
4.1.2.3 Alkyl Aryl Sulfides
4.1.2.4 Dialkyl Sulfides
4.2 Bromination of Alkyl Aryl and Alkyl Benzyl Sulfides
4.3 Acylation of Alkyl Aryl Sulfides
4.4 Hydrolysis of S-Aryl Thioacylates
4.4.1 The Effect of Leaving Group (Arylthioanion) on Kinetics of Alkaline Hydrolysis of S-Aryl Thioacylates
4.4.2 The Effect of Acyl Group on Alkaline Hydrolysis of S-Aryl Thioacylates
4.4.3 The Combined Effects of Structure, Medium and Temperature on Alkaline Hydrolysis of S-aryl Thioacylates in Aqueous-Ethanol Mixtures
4.4.4 Alkaline Hydrolysis of Aryl Thioacylates in Aqueous–Organic Solvents
4.5 Other Reactions Involving Aromatic Thiols and Their Derivatives
4.5.1 Free Radical Reactions
4.5.1.1 Oxidation Reactions
4.5.1.2 Photorearrangement and Addition Reactions
4.5.2 Ionic Reactions
4.5.3 Transition Metal-Catalyzed Reactions
References
5 Acylated Aromatic Sulfides in Organic Synthesis
5.1 Synthesis of Oximes of Acylated Aromatic Sulfides
5.2 Alkylthioaryl Pyrroles
5.2.1 Synthesis from (Alkylthio)aryl Alkyl Ketoximes and Acetylene
5.2.2 Synthesis from (Alkylthio)aryl Alkyl Ketoximes and Vinyl Chloride
5.2.3 Synthesis from (Alkylthio)aryl Alkyl Ketoximes and Dihaloalkanes
5.2.4 Structure and Physical–chemical Characteristics of 2-(4-(Alkylthio)phenyl)pyrroles
5.2.5 Addition of Aryl Thiols to N-vinylpyrroles
5.3 Examples of Syntheses
5.3.1 (Alkylthio)aryl Ketoximes
5.3.2 Pyrroles and N-vinyl Pyrroles
5.3.3 Addition of Thiophenols to N-vinylpyrroles [52]
References
6 Electronic and Conformational Structure of Aromatic Thiols and Their Derivatives
6.1 1H, 13C, 17O, 19F, 33S NMR Spectra
6.1.1 1H and 33S NMR Spectra of Aromatic Thiols
6.1.2 13C NMR Spectra of Aromatic Sulfides
6.1.3 Direct Spin-Spin Coupling Constants 13C–13C of Alkyl Aryl Sulfides
6.1.4 1H, 13C, 19F NMR Spectra of Organyl 4-Fluorophenyl Sulfides
6.1.5 NMR Spectra of Alkyl Aryl Sulfoxides
6.1.6 13C, 17O and 33S NMR Spectra of Alkyl Aryl Sulfones
6.1.7 Conjugation Effects and Conformational Structure in Aromatic Selenides
6.1.8 13C NMR Spectra of Thiobenzoates and Alkyl Benzyl Sulfides
6.2 Effects of Conjugation of the Sulfur Atom
6.2.1 Alkyl Aryl Sulfides
6.2.1.1 Electronic Spectra
6.2.1.2 13C NMR Spectra
6.2.2 Alkyl Aryl Sulfoxides and Sulfones
6.3 Relative Basicity of Alkyl Aryl Sulfides and Some of Their Analogs
6.3.1 Alkyl Phenyl Sulfides
6.3.2 Alkyl Aryl Sulfides
6.3.3 Oxygen and Selenium Analogs of Aromatic Sulfides
6.4 Electronic Effects in S-Aryl Thioacylates and 2-(Arylthio)ethyl Acylates
6.5 35Cl NQR Spectra
6.5.1 Alkyl 4-Chlorophenyl Sulfides
6.5.2 Alkyl 4-Chlorophenyl Sulfoxides and Sulfones
6.6 79/81Br NQR Spectra of Alkyl 4-Bromophenyl Sulfides
6.7 X-Ray Fluorescent Spectra of Aromatic Thiols and Sulfides
6.8 Theoretical Studies of the Structure and Electronic Properties of Aromatic Thiols and Their Derivatives
References
7 Some Areas of Application of Aromatic Thiols and Their Derivatives
7.1 Versatile Reagents
7.2 Advanced Polymers
7.3 Bioorganic and Medical Chemistry
7.4 Optoelectronic Devices
7.5 Additives to Oil Products
7.5.1 Antimicrobial Additives
7.5.2 Anti-wear and Extreme Pressure Additives to Lubricating Oils
7.5.2.1 4-Fluorothiophenol Derivatives
7.5.2.2 Dithiocarboxylic Acid S,S’-Dibenzyl Esters
7.6 2-(4-Ethylthiophenyl)Pyrrole as a Reagent for Palladium Determination
References
Conclusion