Detailed table of contents (pdf)

Table of Contents XV
17.1.2.3.1.3 By Formation of One O—C Bond ............................................ 96
17.1.2.3.1.3.1 Method 1: From (2-Hydroxyaryl)(2-nitroaryl)amines .................... 96
17.1.2.3.1.3.2 Method 2: From Bis(2-alkoxyaryl)amines ............................... 96
17.1.2.3.1.3.3 Method 3: From 2,5-Dianilinobenzo-1,4-quinones ...................... 97
17.1.2.3.1.4 By Formation of One N—C Bond ............................................ 99
17.1.2.3.1.4.1 Method 1: From Diaryl Ethers ......................................... 99
17.1.2.3.1.4.1.1 Variation 1: By Cyclization of 2-Aminoaryl 2-Haloaryl Ethers .............. 99
17.1.2.3.1.4.1.2 Variation 2: By Cyclization of 2-Aminoaryl 2-Nitroaryl Ethers ............ 101
17.1.2.3.1.4.1.3 Variation 3: By Cyclization of 2-Aminoaryl or 2-Nitroaryl Aryl Ethers ..... 101
17.1.2.3.2 Synthesis by Substituent Modification ..................................... 102
17.1.2.3.2.1 Substitution of Existing Substituents ....................................... 102
17.1.2.3.2.1.1 Of Hydrogen ............................................................. 102
17.1.2.3.2.1.1.1 Method 1: By Metalation ............................................. 102
17.1.2.3.2.1.1.2 Method 2: By Friedel–Crafts Acylation, Halogenation, or Nitration ...... 103
17.1.2.3.2.1.1.3 Method 3: By Oxidative Substitution .................................. 104
17.1.2.3.2.1.2 Of Alkyl Groups .......................................................... 105
17.1.2.3.2.1.2.1 Method 1: Demethylation ............................................ 105
17.1.2.3.2.1.3 Of Halogen ............................................................... 105
17.1.2.3.2.1.3.1 Method 1: Reductive Dehalogenation ................................. 105
17.1.2.3.2.2 Modification of Substituents .............................................. 105
17.1.2.3.2.2.1 Method 1: Reductive O-Methylation of Phenoxazin-3-one .............. 105
17.1.2.4 1,4-Oxaphosphinines and Phenoxaphosphines ............................. 106
17.1.2.4.1 Synthesis by Ring-Closure Reactions ....................................... 106
17.1.2.4.1.1 By Formation of Two O—C Bonds .......................................... 106
17.1.2.4.1.1.1 Method 1: From Phosphorylethenamines ............................. 106
17.1.2.4.1.1.2 Method 2: From Bis(2-oxo-2-phenylethyl)phosphinic acid .............. 106
17.1.2.4.1.2 By Formation of One O—C and One P—C Bond ............................. 107
17.1.2.4.1.2.1 Method 1: From Alkynylphosphines and Bromo Ketones ............... 107
17.1.2.4.1.2.2 Method 2: From 1-Phenyl-2-(triphenylphosphonio)ethenolate ......... 107
17.1.2.4.1.3 By Formation of Two P—C Bonds ........................................... 108
17.1.2.4.1.3.1 Method 1: From Diaryl Ethers ........................................ 108
17.1.2.4.1.3.1.1 Variation 1: From Bis(2-lithiophenyl) Ether ............................. 108
17.1.2.4.1.3.1.2 Variation 2: With Phosphorus Chlorides and Aluminum Trichloride ....... 108
17.1.2.4.1.3.1.3 Variation 3: From Diaryl Ether 2-Diazonium Salts ....................... 109
17.1.2.4.2 Synthesis by Substituent Modification ..................................... 110
17.1.2.4.2.1 Substitution of Existing Substituents ....................................... 110
17.1.2.4.2.1.1 Of Heteroatoms .......................................................... 110
17.1.2.4.2.1.1.1 Method 1: By Reduction of 4-Substituted Oxaphosphinines 4-Oxides ... 110