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L Table of Contents 17.4.6.3.5 Addition Reactions ....................................................... 867 17.4.6.3.5.1 Of Hydrogen .............................................................. 867 17.4.6.3.5.1.1 Method 1: By Reduction of 3-Acetyl-3H-3-benzazepine ................ 867 17.4.6.3.5.2 Of Organic Groups ........................................................ 867 17.4.6.3.5.2.1 Method 1: Quaternization of 1H-3-Benzazepin-2-amine with Iodomethane ............................................. 867 17.4.6.3.6 Modification of Substituents .............................................. 867 17.4.6.3.6.1 Method 1: Acetylation of 4-Bromo-1H-3-benzazepin-2-amine .......... 867 17.4.6.4 5H-Dibenz[b,d]azepines ................................................... 868 17.4.6.4.1 Synthesis by Ring-Closure Reactions ....................................... 868 17.4.6.4.1.1 Method 1: By Intramolecular Cyclization under Friedel–Crafts Conditions 868 17.4.6.4.2 Aromatization ............................................................ 869 17.4.6.4.2.1 Method 1: Manganese(IV) Oxide Oxidation of 5,6-Dihydro-7Hdibenz[b,d]azepin-7-ones .................................. 869 17.4.6.4.2.1.1 Variation 1: Lead(IV) Acetate Oxidation of 5,6-Dihydro-7Hdibenz[b,d]azepin-7-ones .................................. 869 17.4.6.4.3 Synthesis by Substituent Modification ..................................... 870 17.4.6.5 11H-Dibenz[b,e]azepines .................................................. 870 17.4.6.5.1 Synthesis by Ring-Closure Reactions ....................................... 871 17.4.6.5.1.1 By Formation of One N—C and One C—C Bond ............................. 871 17.4.6.5.1.1.1 Method 1: By the Thermal Decomposition of Diphenylmethane-2diazonium Tetrafluoroborates ............................. 871 17.4.6.5.1.2 By Formation of One N—C Bond ........................................... 871 17.4.6.5.1.2.1 Method 1: Reduction–Cyclodehydration of 2-(2-Nitrophenyl)benzophenones ................................................. 871 17.4.6.5.1.3 By Formation of One C—C Bond ........................................... 872 17.4.6.5.1.3.1 Method 1: By Bischler–Napieralski Cyclodehydration .................. 872 17.4.6.5.2 Synthesis by Ring Transformation .......................................... 872 17.4.6.5.2.1 By Ring Enlargement ..................................................... 872 17.4.6.5.2.1.1 Method 1: By Beckmann Rearrangement of 10H-Anthracen-9-one Oximes ................................................... 872 17.4.6.5.2.1.2 Method 2: By the Schmidt Reaction of Anthraquinones ................ 873 17.4.6.5.3 Aromatization ............................................................ 874 17.4.6.5.3.1 Method 1: By Dehydrogenation of 1,4-Dimethyl-6,11-dihydro-5Hdibenz[b,e]azepine ........................................ 874 17.4.6.5.3.2 Method 2: From 6H-Dibenz[b,e]azepin-6-ones ......................... 875 17.4.6.5.4 Synthesis by Substituent Modification ..................................... 875 17.4.6.5.4.1 Substitution of Existing Substituents ....................................... 875 17.4.6.5.4.1.1 Method 1: By Displacement of 2-Halo Substituents .................... 875
Table of Contents LI 17.4.6.5.4.2 Addition Reactions ....................................................... 876 17.4.6.5.4.2.1 Of Hydrogen .............................................................. 876 17.4.6.5.4.2.1.1 Method 1: Reduction without Ring Opening .......................... 876 17.4.6.5.4.2.2 Of Heteroatoms .......................................................... 876 17.4.6.5.4.2.2.1 Method 1: Formation of N-Oxides .................................... 876 17.4.6.5.4.3 Modification of Substituents .............................................. 877 17.4.6.5.4.3.1 Method 1: Substitution of 6-Chloromethyl-11H-dibenz[b,e]azepine ..... 877 17.4.6.6 5H-Dibenz[c,e]azepines ................................................... 877 17.4.6.6.1 Synthesis by Ring-Closure Reactions ....................................... 877 17.4.6.6.1.1 By Formation of Two N—C Bonds .......................................... 877 17.4.6.6.1.1.1 Method 1: By Acid-Mediated Cyclization of 2¢-(Aminoalkyl)biphenyl-2carbaldehydes ............................................ 877 17.4.6.6.1.1.1.1 Variation 1: By Acid-Mediated Cyclization of 2-[2¢-(1,3-Dioxolan-2-yl)- 1,1¢-biphenyl-2-yl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole .... 878 17.4.6.6.1.1.2 Method 2: From 2,2¢-Biphenyldicarboxaldehyde ....................... 879 17.4.6.6.1.1.3 Method 3: Ring Closure of 2¢-(Bromomethyl)biphenyl-2-carbaldehyde with Arylamines under Acidic Conditions ................... 880 17.4.6.6.1.1.3.1 Variation 1: Ring Closure of 2¢-(1-Bromoalkyl)biphenyl-2-carbaldehydes under Basic Conditions .................................... 880 17.4.6.6.1.1.3.2 Variation 2: Ring Closure of [2¢-(Bromomethyl)-4-chloro-1,1¢-biphenyl- 2-yl](2-fluorophenyl)methanone ........................... 880 17.4.6.6.1.2 By Formation of One N—C Bond ........................................... 881 17.4.6.6.1.2.1 Method 1: By 1,7-Electrocyclization of Diene-Conjugated Nitrile Ylides . 881 17.4.6.6.2 Aromatization ............................................................ 883 17.4.6.6.2.1 Method 1: By Elimination from an N-Substituted 6,7-Dihydro-5Hdibenz[c,e]azepine ........................................ 883 17.4.6.6.2.2 Method 2: By Dehydrochlorination ................................... 884 17.4.6.6.2.3 Method 3: Oxidation with Mercury(II) Oxide ........................... 884 17.4.6.6.2.4 Method 4: Via Dibenz[c,e]azepinium Salts ............................. 885 17.4.6.6.3 Synthesis by Substituent Modification ..................................... 885 17.4.6.6.3.1 Substitution of Existing Substituents ....................................... 885 17.4.6.6.3.1.1 Of Hydrogen .............................................................. 885 17.4.6.6.3.1.1.1 Method 1: Deprotonation of 5H-Dibenz[c,e]azepines with Lithium Diisopropylamide ......................................... 885 17.4.6.6.3.1.1.2 Method 2: Aerial Oxidation under Phase-Transfer Conditions ........... 886 17.4.6.6.3.1.2 Of Heteroatoms .......................................................... 887 17.4.6.6.3.1.2.1 Method 1: Introduction of Carbofunctional Groups by the Suzuki Reaction .................................................. 887 17.4.6.7 5H-Dibenz[b,f]azepines ................................................... 887 17.4.6.7.1 Synthesis by Ring-Closure Reactions ....................................... 887
Page 1 and 2: Table of Contents IX Volume 17: Six
Page 3 and 4: 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: Table of Contents XLIX 17.4.6.2.4.2
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 and 56: Table of Contents LXIII 17.7.5.1.2.
Page 57 and 58: Table of Contents LXV 17.8.3.2 Cont
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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