RODD'S CHEMISTRY OF CARBON COMPOUNDS
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1 Supplements to the 2nd Edition of RODD'S CHEMISTRY OF CARBON COMPOUNDS VOLUME I ALIPHATIC COMPOUNDS VOLUME II ALICYCLIC COMPOUNDS VOLUME III AROMATIC COMPOUNDS VOLUME IV HETEROCYCLIC COMPOUNDS VOLUME V MISCELLANEOUS GENERAL INDEX
2 V XI CONTENTS VOLUME IIIA Aromatic Compounds; General Introduction; Mononuclear Hydrocarbons and their halogeno derivatives; and derivatives with nuclear substituents attached through nonmetallic elements from Group VI of the Periodic Table Preface Official publications; scientific Journals and periodicals List of common abbreviations and Symbols used IX XVII XVIII Chapter 1. General Introduction 1. Aromatic character by P.J. Garratt 1 (a) Introduction 1 (b) Two-electron Systems 2 (c) Four-electron Systems 3 (d) Six-electron Systems 6 (e) Eight-electron Systems 7 (f) Ten-electron Systems 7 (g) Systems with more than ten electrons 8 (h) Homoaromaticity and Bicyclohomoaromaticity 9 2. Electrophilic aromatic Substitution by J.H. Ridd 11 (a) Ipso-attack 11 (b) Diffusion control of reaction rates 15 (i) Macroscopic diffusion control, 16 (ii) Microscopic diffusion control, 17 (üi) Pre-association, 18 (c) Mechanisms involving electron transfer Nucleophilic aromatic Substitution by N.B. Chapman 21 (a) General 21 (b) Mechanism of Substitution 22 (i) Unimolecular mechanism, 22 (ii) The elimination-addition mechanism - arynes and hetarynes, 24 (iii) The Sjg2 mechanism, "activated" nucleophilic Substitution and Meisenheimer complex formation, 25 (b) New mechanisms 27 (i) The S RN 1 mechanism, 27 (ii) The S N (ANRORC) mechanism, 28- (c) Photochemical reaction 30 (d) Gas phase reactions 31 (e) Miscellany Homolytic aromatic Substitution by G.H. Williams 33 (a) Alkylation 33 (b) Amination 34 (c) Hydroxylation and related reactions 35 (d) Thienylation 35 (e) Arylation 36 (f) Silylation 43 (g) Acylation 43 (h) Ipso-substitution Formation and fission of the benzene nucleus by N.H. Wilson 47 (a) Formation of the benzene nucleus 47
3 XII (i) Pyrolysis, photolysis, condensation and Polymerisation reactions, 47 (ii) Aromatisation of 6-membered ring Compounds, 55 (iii) Isomerisation of alicyclic Compounds, 57 (iv) Aromatisation of 3,4,5,7, and 8-membered rings, 59 (v) Benzenoid rings from hetrocycles, and related reactions, 63 (b) Fission of the benzene ring 67 Chapter 2. Mononuclear hydrocarbons: Benzene and its Homologous by H. Heaney 1. Nuclear magnetic resonance spectroscopy The formation of benzene derivatives by cyclisation reactions Benzocyclopropenes and benzocyclobutenes Electrophilic addition-with-elimination reactions 80 (a) Protonation reactions 80 (b) Metallation reactions 82 (c) Group IV electrophiles 84 (i) Alkylation reactions, 84 (ii) Chloromethylation reactions, 89 (iii) Acylation reactions, 89 (iv) Formylation reactions, 90 (d) Group V electrophiles 91 (i) Nitration reactions, 91 (ii) Nitrosation reactions, 99 (iii) Azocoupling reactions, 100 (e) Group VI electrophiles 100 (i) Hydroxylation reactions, 100 (ii) Sulphur electrophiles, 102 (f) Group VII electrophiles 103 (i) Fluorination reactions, 105 (ii) Chlorination and bromination reactions, 105 (iii) Iodination reactions, Additions to arenes 108 (i) The reduction of arenes and functional groups, 108 (ii) Thermal cycloaddition reactions, 111 (iii) Photocycloaddition reactions, Valence isomers of arenes Aromatisation and functional group modification reactions Oxidation reactions 136 Chapter 3. Halogen derivatives of benzene and its by W.J. Feast homologues Introduction Nuclear halogen derivatives 142 (a) Methods of preparation 142 (i) Replacement of aromatic hydrogen by halogen, 142 (iv) Replacement of an amino group by halogen, 146 (vi) Replacement of one halogen by another, 147 (vii) Perhalogenation, 147 (xi) Trimerization of alkynes, 148 (b) Properties and reactions 148 (ii) Dehalogenation, 148 (iii) Electrophilic reaction, 150 (iv) Nucleophilic Substitution, 150 (v) Photochemical reactions, 152 (vi) Isomerization reactions, 153 (vii) Radical reactions, Alkylbenzenes with halogen in the side chain 156 (a) Methods of preparation 156 (b) Properties and reactions 158 (i) Benzylic halides, 158 (iv) Compounds with more than one side chain, 159
4 XIII Chapter 4. Nuclear Hydroxy Derivatives of Benzene and Its homologues by J.H.P. Tyman 1. Monohydric phenols 161 (a) Preparation 163 (b) Reactions of the hydroxy group 169 (i) Esterification, 169 (ii) Replacement, 170 (iü) Protection, 171 (c) Reactions of the aromatic ring 172 (i) Protonation and deuteriation, 172 (ii) Electrophilic Substitution, 173- (d) Phenol oxidation 174 (i) Oxidative coupling, 174 (ii) Other oxidations, 178 (iii) Cyclohexadienone formation, 181 (e) Hindered phenols 184 (f) Reactions of alkyl phenols 186 (g) Quinone methides 190 (h) Phenolic aldehydes. Ketones and acids 194 (i) Phenolic ethers 199 (i) Preparation, 199 (ii) Dealkylation. Alkylation and coupling, 201 (iii) Cyclisation and rearrangement, 204 (iv) Electrophilic and nucleophilic Substitution, 207 (j) Halogenophenols 209 (k) Nitrophenols 212 (1) Amino phenols 215 (m) Azo Compounds and diazonium salts 216 (n) Sulphonation and related reactions Dihydric phenols 218 (i) Preparations, 218 (ii) Reactions, 224 (iii) Alkylation, acylation and cyclic products, Polyhydric phenols and their derivatives 237 (i) Natural occurrence, 237 (ii) Reactions, 238 Chapter 5. Mononuclear Hydrocarbons Carrying Substituents through Sulphur and Selenium: Thiophenols, Sulphides, by J.H.P. Tyman Attached etc. Introduction 241 Properties 242 Methods of Preparation 244 Arenethiols or thiophenols 1. Reduction of sulphonyl Chlorides and reactions of sulphenyl halides 244 (a) Sulphonyl Chlorides 244 (b) Sulphenyl Chlorides Reduction of diphenylsulphides From phenols From diazonium salts Formation from phenols and aromatic amines by thiacyanation Formation from aromatic halides 252 (a) Use of alkali metal sulphides 252 (b) Use of heavy metal alkyl sulphides From organometallic Compounds Other methods 257
5 XIV 9. Conversion of the SMe to the thiol group 260 Reactions of thiols 260 (1) Oxidation 260 (a) With halogens 260 (b) By dimethyl and other sulphoxides 264 (c) Use of diethyl azodicarboxylate 265 (d) By N-halo reagents and related Compounds 266 (e) Use of metal ions and oxides 266 (f) By molecular oxygen 267 (2) Substitution reactions 270 (3) Rearrangements 273 (4) General reactions and catalytic uses 278 (5) Nucleophilic reactions 280 (a) Alicyclic and acyclic examples 281 (b) Aromatic and heterocyclic examples 286 (c) Dealkylation and deacylation reactions 289 (d) Addition processes 291 (i) Alkenes and alkynes, 291 (ii) Carbonyl Compounds, 294 (iii) Conjugated Systems, 295 (iv) Alkylene oxides, 298 (6) Synthetic uses of aromatic thiols 299 (a) Unsaturated hydrocarbons 299 (b) Carbonyl Compounds and derivatives 302 (c) Alcohols and amines 305 (d) Use of selenophenol derivatives 307 Sulphides 310 (1) Saturated alkyl, aryl and diaryl Compounds 310 (a) Preparation 310 (i) By alkylation, 310 (ii) From disulphides and thiolcarbonates, 312 (iii) By reduction, 313 (iv) From thiocarbonyl Compounds, 314- (b) Reactions 315 (i) Substitution, 315 (ii) Oxidation, 316 (iii) Rearrangement, 316- (c) Synthetic uses of thioethers 319 (i) Phenyl methyl sulphide (and its derivatives), 320 (ii) Chloromethyl phenyl sulphide and derivatives, 322 (2) Thioacetals and related Compounds 323 (a) Preparation 324 (b) Synthetics uses of thioacetals 326 (c) Synthetic uses of tris(arylthio)methanes 330 (3) Unsaturated sulphides 332 (a) Preparation 332 (b) Synthetic uses of unsaturated sulphides 335 (4) Benzylic sulphides 338 Chapter 6. Mononuclear Hydrocarbons Carrying Nuclear Substituents Containing Sulphur: Sulphonic Acids, Sulphonic Acids, and Sulphenyl Compounds of the Benzene Series by G.C. Barrett 1. Nuclear sulphonic acids of benzene and its homologues; arene sulphonic acids 341 (a) Preparation 341 (i) Direct sulphonation, 341 (ii) Indirect sulphonation, 342
6 XV (b) General properties and reactions 343 (c) Sulphonicanhydrides ArSOj-0-SOj and ArS0 3 -O-COR 343 (d) Sulphonyl peroxides ArS0 2-0'OS0 2 R and ArSOj-0-O-COR 344 (e) Sulphonate esters 344 (f) Sulphonyl halides 346 (g) Sulphonamides 347 (h) Structural relatives of sulphonamides; sulphonylheterocumulenes 352 (i) Sulphonyl cyanides Nuclear sulphinic acids of benzene and its homologues; arene sulphinic acids 355 (a) Preparation 355 (b) General properties and reactions 356 (c) Sulphinate esters 357 (d) Sulphinamides 359 (e) Sulphinyl azides 361 (f) Sulphinyl sulphones Nuclear sulphenic acids of benzene and its homologues arene sulphenic acids 361 (a) Preparation 361 (b) Sulphenyl halides 362 (c) Sulphenate esters 363 (d) Sulphenamides 365 (e) Thionitrites and thionitrates Nuclear thiolsulphonic and thiolsulphinic acids of benzene and its homologues; arenethiolsulphonic and arenethiolsulphinic acids 366 (a) Arenethiolsulphonate esters 367 (b) Arenethiolsulphinate esters 368 Chapter 7. Mononuclear hydrocarbons carrying nuclear containing selenium or tellurium by P.G. Harrison substituents 1. Introduction Selenium 371 (a) Arylselenium(II) Compounds ' 371 (b) The selenoxide elimination and related reactions 384 (c) Arylselenium(IV) Compounds Tellurium 391 (a) Aryltellurium(II) Compounds 391 (b) Aryltellurium(IV) Compounds 396 Index 403
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