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LXIV Table of Contents 17.8.1.1.3.1 Method 1: Oxobilanes .............................................. 1104 17.8.1.1.3.1.1 Variation 1: a-Oxobilanes ............................................. 1104 17.8.1.1.3.1.2 Variation 2: b-Oxobilanes ............................................ 1105 17.8.1.1.3.2 Method 2: b-Bilenes ................................................ 1106 17.8.1.1.3.2.1 Variation 1: 1,19-Dimethyl-b-bilenes .................................. 1106 17.8.1.1.3.2.2 Variation 2: b-Bilene-1,19-dicarboxylates .............................. 1107 17.8.1.1.3.3 Method 3: a,c-Biladienes ............................................ 1108 17.8.1.1.3.3.1 Variation 1: Symmetrical 1,19-Dimethyl-a,c-biladiene Salts ............. 1108 17.8.1.1.3.3.2 Variation 2: Unsymmetrical 1,19-Dimethyl-a,c-biladiene Salts .......... 1110 17.8.1.1.3.3.3 Variation 3: 1-Bromo-19-methyl-a,c-biladiene Salts .................... 1115 17.8.1.2 Syntheses of Porphyrins .................................................. 1116 17.8.1.2.1 Method 1: From Monopyrrole Tetramerization ....................... 1116 17.8.1.2.2 Method 2: From Dipyrrolic Intermediates: The [2+2] Routes .......... 1124 17.8.1.2.2.1 Variation 1: Using Dipyrromethenes .................................. 1126 17.8.1.2.2.2 Variation 2: Using Dipyrromethanes .................................. 1129 17.8.1.2.2.3 Variation 3: Using Dipyrroketones .................................... 1135 17.8.1.2.3 Method 3: From Tripyrrolic Intermediates: The [3 +1] Route ........... 1138 17.8.1.2.3.1 Variation 1: Using a Tripyrrane and a 2,5-Diformyl-1H-pyrrole .......... 1139 17.8.1.2.3.2 Variation 2: Using a Tripyrrane and a 2,5-Bis[(dimethylamino)methyl]- 1H-pyrrole ............................................... 1141 17.8.1.2.4 Method 4: From Open-Chain Tetrapyrrolic Intermediates ............. 1143 17.8.1.2.4.1 Variation 1: Using a-Oxobilanes ....................................... 1145 17.8.1.2.4.2 Variation 2: Using b-Oxobilanes ...................................... 1147 17.8.1.2.4.3 Variation 3: Using 1,19-Dimethyl-b-bilenes ............................ 1148 17.8.1.2.4.4 Variation 4: Using b-Bilene-1,19-diesters .............................. 1149 17.8.1.2.4.5 Variation 5: Using Other b-Bilenes .................................... 1150 17.8.1.2.4.6 Variation 6: Using 1,19-Dimethyl-a,c-biladienes ........................ 1151 17.8.1.2.4.7 Variation 7: Using 1-Bromo-19-methyl-a,c-biladienes .................. 1159 17.8.1.2.4.8 Variation 8: Using Other a,c-Biladienes ................................ 1159 17.8.2 Product Subclass 2: Reduced Porphyrins ................................ 1161 17.8.2.1 Chlorins (b,b¢-Dihydroporphyrins) ........................................ 1161 17.8.2.1.1 Method 1: By Ring Synthesis ........................................ 1161 17.8.2.1.2 Method 2: By Reduction of Porphyrins or Metal Porphyrinates ......... 1165 17.8.2.1.3 Method 3: By Oxidation of Porphyrins or Metal Porphyrinates ......... 1171 17.8.2.2 Bacteriochlorins and Isobacteriochlorins (b,b¢,b¢¢,b¢¢¢-Tetrahydroporphyrins) 1173 17.8.2.3 Syntheses of Benzoporphyrins ............................................ 1174 17.8.2.3.1 Method 1: Tetrabenzoporphyrins .................................... 1175 17.8.2.3.2 Method 2: Monobenzoporphyrins, Dibenzoporphyrins, and Benzoporphyrin Derivatives ............................... 1178 17.8.3 Product Subclass 3: Isomeric, Contracted, and Expanded Porphyrin Systems ..................................................... 1180 17.8.3.1 Syntheses of [18]Porphyrin (1,1,1,1) Isomers ............................... 1180 17.8.3.1.1 Method 1: Porphycene {[18]Porphyrin (2,0,2,0)} ...................... 1180 17.8.3.1.2 Method 2: Corrphycene (Porphycerin) {[18]Porphyrin (2,1,0,1)} ........ 1181
Table of Contents LXV 17.8.3.2 Contracted Porphyrins: Syntheses of Corroles ............................. 1182 17.8.3.2.1 Method 1: From Monopyrroles ...................................... 1182 17.8.3.2.1.1 Variation 1: Using 2-Substituted 1H-Pyrroles .......................... 1182 17.8.3.2.1.2 Variation 2: Using 2,5-Di-unsubstituted 1H-Pyrroles and Aldehydes ..... 1183 17.8.3.2.2 Method 2: From Dipyrroles .......................................... 1183 17.8.3.2.3 Method 3: From a,c-Biladiene Salts .................................. 1184 17.8.3.2.4 Method 4: By Porphyrin Ring Contraction ............................ 1186 17.8.3.3 Expanded Porphyrins .................................................... 1186 17.8.3.3.1 Method 1: Syntheses of Sapphyrins .................................. 1187 17.8.3.3.1.1 Variation 1: The [3+2] Approach ..................................... 1187 17.8.3.3.1.2 Variation 2: The [3+(1) 2 ] Approach ................................... 1188 17.8.3.3.1.3 Variation 3: The [4 +1] Approach ..................................... 1189 17.8.3.3.1.4 Variation 4: The [1] 5 Approach ........................................ 1191 17.8.3.3.2 Method 2: Syntheses of Pentaphyrins ................................ 1191 17.8.4 Reactions around the Porphyrin Periphery ................................ 1192 17.8.4.1 Method 1: Electrophilic Substitution Reactions ....................... 1192 17.8.4.1.1 Variation 1: Halogenation ............................................ 1193 17.8.4.1.2 Variation 2: Nitration ................................................ 1197 17.8.4.1.3 Variation 3: Formylation and Acylation ................................ 1199 17.8.4.1.4 Variation 4: Peripheral Metalation .................................... 1208 17.8.4.1.5 Variation 5: Reactions with Carbenes and Nitrenes ..................... 1210 17.8.4.2 Method 2: Reactions with Nucleophiles .............................. 1211 17.8.4.3 Method 3: Oxidation Reactions ...................................... 1216 17.8.4.4 Method 4: Cycloaddition Reactions .................................. 1217 17.8.4.4.1 Variation 1: Intermolecular Reactions ................................. 1217 17.8.4.4.2 Variation 2: Intramolecular Reactions ................................. 1218 17.9 Product Class 9: Phthalocyanines and Related Compounds N. B. McKeown 17.9 Product Class 9: Phthalocyanines and Related Compounds 1237 17.9.1 Product Subclass 1: Metal-Free Phthalocyanine ......................... 1245 17.9.1.1 Method 1: From Phthalonitrile ....................................... 1245 17.9.1.1.1 Variation 1: From Generation and Demetalation of a Labile Metal Complex ................................................. 1246 17.9.1.2 Method 2: From Isoindolinediimine .................................. 1246 17.9.2 Product Subclass 2: Metal–Phthalocyanine Complexes .................. 1247 17.9.2.1 Method 1: From Phthalonitrile ....................................... 1249 17.9.2.2 Method 2: From Phthalic Anhydride ................................. 1253 17.9.2.3 Method 3: From Phthalimide ........................................ 1254 17.9.2.4 Method 4: From Isoindolinediimine .................................. 1254 17.9.2.5 Method 5: From 2-Cyanobenzamide ................................. 1255 17.9.2.6 Method 6: From Phthalocyanine ..................................... 1256 17.9.2.7 Method 7: Metal Exchange of Dilithium or Disodium Complex ........ 1257
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Table of Contents IX Volume 17: Six
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Table of Contents XI Table of Conte
Page 5 and 6: Table of Contents XIII 17.1.1.2.4.1
Page 7 and 8: Table of Contents XV 17.1.2.3.1.3 B
Page 9 and 10: Table of Contents XVII 17.1.3.2 1,4
Page 11 and 12: Table of Contents XIX 17.1.3.3.1.1.
Page 13 and 14: Table of Contents XXI 17.2 Product
Page 15 and 16: Table of Contents XXIII 17.2.1.2.1.
Page 17 and 18: Table of Contents XXV 17.2.1.3.1.1
Page 19 and 20: Table of Contents XXVII 17.2.2 Prod
Page 21 and 22: Table of Contents XXIX 17.2.2.1.3.3
Page 23 and 24: Table of Contents XXXI 17.2.2.2.1.4
Page 25 and 26: Table of Contents XXXIII 17.2.3.1.1
Page 27 and 28: Table of Contents XXXV 17.2.3.1.2.2
Page 29 and 30: Table of Contents XXXVII 17.2.3.1.4
Page 31 and 32: Table of Contents XXXIX 17.3.3.2 Sy
Page 33 and 34: Table of Contents XLI 17.4.2.2.2.2
Page 35 and 36: Table of Contents XLIII 17.4.4.1.2.
Page 37 and 38: Table of Contents XLV 17.4.5.1.2.3
Page 39 and 40: Table of Contents XLVII 17.4.5.4.1.
Page 41 and 42: Table of Contents XLIX 17.4.6.2.4.2
Page 43 and 44: Table of Contents LI 17.4.6.5.4.2 A
Page 45 and 46: Table of Contents LIII 17.4.6.7.4.4
Page 47 and 48: Table of Contents LV 17.5.2.2.1 Met
Page 49 and 50: Table of Contents LVII 17.6.2.1.1.4
Page 51 and 52: Table of Contents LIX 17.6.5.2.2.1.
Page 53 and 54: Table of Contents LXI 17.7.3.2 [2.3
Page 55: Table of Contents LXIII 17.7.5.1.2.
Page 59 and 60: Table of Contents LXVII 17.9.8.3 Me
Page 61: Table of Contents LXIX 17.9.22.3 Me
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