Introduction
Chapter 1. Synthesis of aromatic thiols
1.1. Reactions of aromatic thiols 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
Chapter2. Aromatic sulfides
2.1. General approaches to synthesis of aryl sulfides
2.2. Catalytic 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 disulfides
2.4.6. Functionally substituted alkyl aryl sulfides
References
Chapter 3. Aromatic sulfoxides, sulfones and other derivatives of aromatic thiols
3.1. Aromatic sulfoxides
3.2. Aromatic sulfones 3.3. alkyl benzyl sulfones
3.4. S-Alkyl, S-aryl, S-benzylthioacelates and organylthiobenzoates
3.5. 2-Arylthioethylacylates
3.6. Dithiocarboxylic acid dibenzyl esters
3.7. Derivatives of aromatic selenols
3.8. Examples of syntheses
3.8.1. Synthesis of aromatic sulfoxides
3.8.2. Alkyl aryl sulfones
3.8.3. Alkyl-, aryl-, and benzylthioacelates
3.8.4. Dibenzyl ethers of dithiocarboxylic acids
3.8.5. Derivatives of aromatic selenols
References
Chapter4. 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 thioanizoles
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-arylthioacylates
4.4.1. Effect of leaving group (arylthioanion) on kinetics of alkaline hydrolysis of S-arylthioacetates
4.4.2. Effect of acyl group on alkaline hydrolysis of S-arylthioacylates
4.4.3. Combined effects of structure, medium and temperature on alkaline hydrolysis of S-arylthioacylates in aqueous-ethanol mixtures
4.4.4. Alkaline hydrolysis of arylthioacylates 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
Chapter 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 alkylthioarylalkyl ketoximes and acetylene
5.2.2. Synthesis from alkylthioarylalkyl ketonoximes and vinyl chloride
5.2.3. Synthesis from alkylthioarylalkyl ketonoximes and dihalides
5.2.4. Structure and physical-chemical characteristics of 2-(4-alkylthiophenyl) pyrroles
5.2.5. Addition of aryl thiols to N-vinylpyrroles
5.3. Examples of syntheses
5.3.1. Synthesis of alkylthioaryl ketonoximes
5.3.2. Pyrroles and N-vinylpyrroles
5.3.3. Addition of thiophenols to N-vinylpyrroles
References
Chapter 6. Electronic and conformational structure of aromatic thiols and their derivatives
6.1. 1H, 13C, 17O, 19F, 33S NMR spectra
6.1.1. 1 NMR spectra of aromatic thiols
6.1.2. 13 NMR spectra of aromatic sulfides
6.1.3. Direct spin-spin coupling constants 13C-13 of alkyl aryl sulfides
6.1.4. 1 , 13 , 19F NMR spectra of organyl-4-fluorophenylsulfides
6.1.5. 13 , 17 and 33S NMR spectra of alkyl aryl sulfides
6.1.6. Conjugation effects and conformational structure in aromatic selenides
6.1.7. 13 NMR spectra of thiobenzoates and alkyl benzyl sulfides
6.2. Electronic spectra
6.2.1. Alkyl aryl sulfides
6.2.2. Alkyl aryl sulfoxides and sulfones
6.3. Relative basicity of alkyl aryl sulfides and their analogues
6.3.1. Phenyl sulfides
6.3.2. Alkyl aryl sulfides
6.3.3. Oxygen and selenium analogues of aromatic sulfides
6.4. IR spectra of arylthioacetates
6.5. 35Cl NQR spectra
6.5.1. Alkyl-4-chlorophenylsulfides
6.5.2. Alkyl-4-chlorophenylsulfoxides and sulfones
6.6. 79Br and 81Br NQR spectra of alkyl-(4-bromophenyl)sulfides
6.7. X-ray fluorescence spectra of aromatic thiols and sulfides
References
Chapter 7. Some areas of application of aromatic thiols and their derivatives
7.1. Aromatic thiols
7.2. Aromatic sulfides
7.3. Aromatic sulfones
7.4. Additives to oil products
7.4.1. Antimicrobial additives
7.4.2. Anti-wear and extreme pressure additives to lubricating oils
7.4.2.1. 4-Fluorothiophenol derivatives
7.4.2.2. Dithiocarboxylic acid S,S-dibenzyl esters
7.5. 2-(4-Ethylthiophenyl)pyrrole as reagent for Pd determination
References
Conclusion
