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LII Table of Contents 17.4.6.7.1.1 By Formation of Two C—C Bonds .......................................... 888 17.4.6.7.1.1.1 Method 1: From 2,2¢-Bis(bromomethyl)diphenylamine ................ 888 17.4.6.7.1.1.1.1 Variation 1: From Bis(2¢-formylphenyl)amine ........................... 888 17.4.6.7.2 Synthesis by Ring Transformation .......................................... 888 17.4.6.7.2.1 By Ring Enlargement ..................................................... 888 17.4.6.7.2.1.1 Method 1: From 1-Arylindoles ........................................ 888 17.4.6.7.2.1.2 Method 2: From 9,10-Dihydroacridin-9-ylmethanol .................... 890 17.4.6.7.2.1.2.1 Variation 1: From 9-(Hydroxymethyl)-9,10-dihydroacridine and Sulfuric Acid ...................................................... 891 17.4.6.7.2.1.2.2 Variation 2: Base-Promoted Ring Expansion of Acridine Methanesulfonates ................................................ 892 17.4.6.7.3 Aromatization ............................................................ 893 17.4.6.7.3.1 Method 1: Bromination–Dehydrobromination ......................... 893 17.4.6.7.3.2 Method 2: Catalytic Dehydrogenation ................................ 893 17.4.6.7.4 Synthesis by Substituent Modification ..................................... 894 17.4.6.7.4.1 Substitution of Existing Substituents ....................................... 894 17.4.6.7.4.1.1 Of Hydrogen .............................................................. 894 17.4.6.7.4.1.1.1 Method 1: Nitration of 5H-Dibenz[b,f]azepines ........................ 894 17.4.6.7.4.1.1.2 Method 2: Friedel–Crafts Acylation of 5-Acyl-5H-dibenz[b,f]azepines ... 895 17.4.6.7.4.1.1.3 Method 3: N-Alkylation of 5H-Dibenz[b,f]azepines ..................... 895 17.4.6.7.4.1.1.3.1 Variation 1: By Phase-Transfer Catalysis ................................ 896 17.4.6.7.4.1.1.3.2 Variation 2: By Reductive Amination ................................... 896 17.4.6.7.4.1.1.4 Method 4: N-Acylation of 5H-Dibenz[b,f]azepines ..................... 897 17.4.6.7.4.1.1.5 Method 5: Chlorocarbonylation of 5H-Dibenz[b,f]azepines with Phosgene Equivalents ..................................... 897 17.4.6.7.4.1.1.5.1 Variation 1: Reaction with Cyanogen Bromide .......................... 898 17.4.6.7.4.2 Of Metals ................................................................ 898 17.4.6.7.4.2.1 Method 1: Directed ortho-Metalation ................................. 898 17.4.6.7.4.3 Of Heteroatoms .......................................................... 899 17.4.6.7.4.3.1 Method 1: By Halogen–Lithium Exchange ............................. 899 17.4.6.7.4.3.2 Method 2: Nucleophilic Displacement of Bromide ..................... 900 17.4.6.7.4.3.2.1 Variation 1: Nucleophilic Displacement of Bromide by Nitrogen Nucleophiles (Aminodebromination) ....................... 900 17.4.6.7.4.4 Addition Reactions ....................................................... 901 17.4.6.7.4.4.1 Reduction Reactions ...................................................... 901 17.4.6.7.4.4.1.1 Method 1: Reduction at the C10—C11 Double Bond ................... 901 17.4.6.7.4.4.2 Of Heteroatoms .......................................................... 901 17.4.6.7.4.4.2.1 Method 1: Halogenation ............................................. 901 17.4.6.7.4.4.3 Oxidation Reactions ...................................................... 902 17.4.6.7.4.4.3.1 Method 1: Formation of N-Oxides .................................... 902 17.4.6.7.4.4.3.2 Method 2: Formation of Epoxides .................................... 902
Table of Contents LIII 17.4.6.7.4.4.4 Cycloadditions ............................................................ 903 17.4.6.7.4.4.4.1 Method 1: Cyclopropanation by the Simmons–Smith Reaction ......... 903 17.4.6.7.4.4.4.1.1 Variation 1: Cyclopropanation with Dichlorocarbene .................... 904 17.4.6.7.4.4.4.2 Method 2: 1,3-Dipolar Cycloaddition with Diarylnitrilimines ............ 904 17.4.6.7.4.4.4.3 Method 3: [2 +2] Photodimerization of 5-Acetyl-5H-dibenz[b,f]azepine . 904 17.4.6.7.4.4.4.4 Method 4: [4 +2] Cycloaddition of Dibenzazepynes .................... 905 17.4.6.8 9H-Tribenz[b,d,f]azepines ................................................. 906 17.4.6.8.1 Synthesis by Ring-Closure Reactions ....................................... 906 17.4.6.8.1.1 By Formation of One N—C Bond ........................................... 906 17.4.6.8.1.1.1 Method 1: From N,N-Diphenyl-1,1¢-biphenyl-2,2¢-diamine .............. 906 17.4.6.8.1.2 By Annulation to a Preformed System ..................................... 907 17.4.6.8.1.2.1 Method 1: From 5-Acetyl-10-bromo-5H-dibenz[b,f]azepine and Furan .. 907 17.4.6.8.1.2.1.1 Variation 1: From 5-Acetyl-10-bromo-5H-dibenz[b,f]azepine and Cyclohexa-1,3-diene ....................................... 908 17.4.6.8.2 Synthesis by Substituent Modification ..................................... 909 17.4.6.9 Other Group 15 Benzoheterepins .......................................... 910 17.4.6.9.1 1H-1-Benzoheterepins .................................................... 910 17.4.6.9.1.1 Synthesis by Ring-Closure Reactions ....................................... 911 17.4.6.9.1.1.1 Method 1: Thermal Valence Isomerization of Dihydrocyclobut[b]heteroindoles ................................................... 911 17.4.6.9.1.1.2 Method 2: From [(1Z,3Z)-1-Bromo-4-(2-bromophenyl)buta-1,3dien-1-yl](trimethyl)silane ................................. 912 17.4.6.9.2 3-Benzoheterepins ....................................................... 914 17.4.6.9.2.1 Synthesis by Ring-Closure Reactions ....................................... 914 17.4.6.9.2.1.1 Method 1: Potassium Hydroxide/18-Crown-6 Catalyzed Addition of Phenylphosphine to 1,2-Diethynylbenzene ................. 914 17.4.6.9.2.1.2 Method 2: From (Z,Z)-2-Bis(b-bromovinyl)benzene .................... 914 17.4.6.9.3 Dibenzo[b,d]heterepins ................................................... 916 17.4.6.9.3.1 Synthesis by Ring-Closure Reactions ....................................... 916 17.4.6.9.3.1.1 Method 1: From [(Z)-1-Bromo-2-(2¢-bromo-1,1¢-biphenyl- 2-yl)vinyl](trimethyl)silane ................................. 916 17.4.6.9.4 Dibenzo[b,f]heterepins ................................................... 917 17.4.6.9.4.1 Synthesis by Ring-Closure Reactions ....................................... 917 17.4.6.9.4.1.1 Method 1: From 1-Bromo-2-[(Z)-2-(2-bromophenyl)vinyl]benzene ...... 917 17.4.6.9.5 Tribenzo[b,d,f]heterepins ................................................. 918 17.4.6.9.5.1 Synthesis by Ring-Closure Reactions ....................................... 918 17.4.6.9.5.1.1 Method 1: Transition-Metal-Catalyzed Trimerization of Phenyl{bis[2- (phenylethynyl)phenyl]}phosphine Oxide ................... 918 17.4.6.9.6 Reactions of Other Group 15 Benzoheterepins ............................. 920
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 and 42: Table of Contents XLIX 17.4.6.2.4.2
Page 43: Table of Contents LI 17.4.6.5.4.2 A
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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