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XII Table of Contents 17.1.1.2.1.1.2.2.1 Method 1: Reaction of Spiroepoxyhexadienones with Pentahalobenzenethiols .................................... 28 17.1.1.2.1.1.2.2.2 Method 2: Autocondensation Reaction of a Sulfonated a-Tetralone Derivative ................................................. 29 17.1.1.2.1.1.2.3 Fragments C—C—O—C—C and S ............................................ 30 17.1.1.2.1.1.2.3.1 Method 1: Reaction of Diaryl Ether with Sulfur (The Ferrario Reaction) ... 30 17.1.1.2.1.1.2.3.1.1 Variation 1: Reaction of Diaryl Ether with Sulfur Dichloride ............... 31 17.1.1.2.1.1.2.3.1.2 Variation 2: Reaction of Diaryl Ether with Sulfur Dication ................. 31 17.1.1.2.1.1.2.4 Fragments C—C—S—C—C and O ............................................ 31 17.1.1.2.1.1.2.4.1 Method 1: Reaction of Bis(chloroaryl) Sulfide with Oxygen Divalent Nucleophiles ............................................... 31 17.1.1.2.1.1.2.4.2 Method 2: Reaction of Bis(dihydroxyphenyl) Sulfone with Oxidant ....... 32 17.1.1.2.1.1.3 By Formation of One Heteroatom—Carbon Bond ............................ 32 17.1.1.2.1.1.3.1 Fragment S—C—C—O—C—C ................................................ 32 17.1.1.2.1.1.3.1.1 Method 1: Cyclization of a 1,2-S,O-Substituted Diaryl Ether ............. 32 17.1.1.2.1.1.3.2 Fragment O—C—C—S—C—C ................................................ 33 17.1.1.2.1.1.3.2.1 Method 1: Alkylative Cyclization of 2-(Arylsulfonyl)ethanone ............ 33 17.1.1.2.1.1.3.2.2 Method 2: Cyclization of Diaryl Sulfides and Sulfoxides ................. 34 17.1.1.2.1.2 By Annulation to the Heterocyclic Ring ..................................... 35 17.1.1.2.1.2.1 Method 1: Annulation of Heterocycles ................................. 35 17.1.1.2.1.2.2 Method 2: Annulation of Carbocycles .................................. 36 17.1.1.2.2 Synthesis by Ring Transformation ........................................... 36 17.1.1.2.2.1 Method 1: Ring Enlargement .......................................... 36 17.1.1.2.2.2 Method 2: Formal Exchange of Ring Members with Retention of the Ring Size ....................................................... 38 17.1.1.2.3 Aromatization ............................................................. 38 17.1.1.2.3.1 Method 1: Elimination from 2,3-Dihydro-1,4-benzoxathiins ............. 38 17.1.1.2.4 Synthesis by Substituent Modification ...................................... 39 17.1.1.2.4.1 Substitution of Existing Substituents ........................................ 39 17.1.1.2.4.1.1 Of Hydrogen ............................................................... 39 17.1.1.2.4.1.1.1 Method 1: C-Formylation of 1,4-Benzoxathiins ......................... 39 17.1.1.2.4.1.1.2 Method 2: Electrophilic Substitution of Phenoxathiin ................... 39 17.1.1.2.4.1.2 Of Metals ........................................................... 42 17.1.1.2.4.1.2.1 Method 1: Substitution Reactions Involving Organolithium Derivatives .. 42 17.1.1.2.4.1.2.2 Method 2: Substitution Reactions Involving Transition-Metal Complexes . 45 17.1.1.2.4.1.3 Of Carbon Functionalities .................................................. 45 17.1.1.2.4.1.3.1 Method 1: Reactions Involving Rearrangement of Nitrogen onto an Annulated Ring Carbon ..................................... 45 17.1.1.2.4.1.3.2 Method 2: Reactions Involving Decarboxylation at an Annulated Ring Carbon ............................................... 46
Table of Contents XIII 17.1.1.2.4.1.3.3 Method 3: Reactions Involving Dealkylation at the Ring Sulfur ........... 46 17.1.1.2.4.1.4 Of Heteroatoms ........................................................... 46 17.1.1.2.4.1.4.1 Method 1: Replacement of Heteroatoms on an Annulated Ring Carbon .. 46 17.1.1.2.4.1.4.2 Method 2: Removal of Oxygen from the Ring Sulfur or from an Annulated Ring Nitrogen .............................................. 47 17.1.1.2.4.2 Addition Reactions ........................................................ 48 17.1.1.2.4.2.1 Method 1: Reactions of Phenoxathiins with Alkylating Reagents ......... 48 17.1.1.2.4.2.2 Method 2: Reactions Involving Phenoxathiin Cation Radical ............. 49 17.1.1.2.4.2.3 Method 3: Oxidation of a Ring Sulfur .................................. 49 17.1.1.2.4.3 Rearrangement of Substituents ............................................ 50 17.1.1.2.4.3.1 Method 1: Reactions Involving Benzyne ................................ 50 17.1.1.2.4.4 Modification of Substituents ............................................... 51 17.1.1.2.4.4.1 Method 1: Reactions Involving Acyl Groups ............................ 51 17.1.2 Product Subclass 2: One Oxygen and One Nitrogen or Phosphorus Atom H. Ulrich 17.1.2 Product Subclass 2: One Oxygen and One Nitrogen or Phosphorus Atom . 55 17.1.2.1 1,4-Oxazines ............................................................... 55 17.1.2.1.1 Synthesis by Ring-Closure Reactions ........................................ 55 17.1.2.1.1.1 By Formation of One O—C and One N—C Bond .............................. 55 17.1.2.1.1.1.1 Method 1: From N-Phenacylideneaniline ............................... 55 17.1.2.1.1.2 By Formation of One O—C Bond ............................................ 56 17.1.2.1.1.2.1 Method 1: From N,N-Diphenacylaniline ................................ 56 17.1.2.1.1.2.2 Method 2: From a-Aminocarboxylic Acid Derivatives ................... 56 17.1.2.1.1.3 By Formation of One N—C Bond ............................................ 57 17.1.2.1.1.3.1 Method 1: From Bis(b-oxoethyl) Ethers and Related Compounds ........ 57 17.1.2.1.2 Synthesis by Ring Transformation ........................................... 58 17.1.2.1.2.1 Method 1: From 1,4-Dioxanes ......................................... 58 17.1.2.2 1,4-Benzoxazines .......................................................... 58 17.1.2.2.1 Synthesis by Ring-Closure Reactions ........................................ 59 17.1.2.2.1.1 By Formation of One O—C and One N—C Bond .............................. 59 17.1.2.2.1.1.1 Method 1: From Sulfinylamines and Ynamines ......................... 59 17.1.2.2.1.1.2 Method 2: From Benzo-1,2-quinone Imines and Ynamines .............. 60 17.1.2.2.1.1.3 Method 3: From Aminophenols and a-Carbonyl Compounds ............ 61 17.1.2.2.1.1.3.1 Variation 1: From a-Halo Esters ......................................... 61 17.1.2.2.1.1.3.2 Variation 2: From a-Halo Ketones ...................................... 62 17.1.2.2.1.1.3.3 Variation 3: From Maleic Anhydride ..................................... 63 17.1.2.2.1.1.3.4 Variation 4: From Ynones, Dimethyl 3-Methoxy-2-oxobutane-1,4-dioate, or Ethyl Ethoxy(imino)acetate ................................. 63 17.1.2.2.1.1.3.5 Variation 5: From a-Carbonyl Compounds .............................. 64
Page 1 and 2: Table of Contents IX Volume 17: Six
Page 3: Table of Contents XI Table of Conte
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
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Table of Contents LXIII 17.7.5.1.2.
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Table of Contents LXV 17.8.3.2 Cont
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Table of Contents LXVII 17.9.8.3 Me
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Table of Contents LXIX 17.9.22.3 Me
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