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XII Table <strong>of</strong> Contents<br />

17.1.1.2.1.1.2.2.1 Method 1: Reaction <strong>of</strong> Spiroepoxyhexadienones with<br />

Pentahalobenzenethiols .................................... 28<br />

17.1.1.2.1.1.2.2.2 Method 2: Autocondensation Reaction <strong>of</strong> a Sulfonated a-Tetralone<br />

Derivative ................................................. 29<br />

17.1.1.2.1.1.2.3 Fragments C—C—O—C—C and S ............................................ 30<br />

17.1.1.2.1.1.2.3.1 Method 1: Reaction <strong>of</strong> Diaryl Ether with Sulfur (The Ferrario Reaction) ... 30<br />

17.1.1.2.1.1.2.3.1.1 Variation 1: Reaction <strong>of</strong> Diaryl Ether with Sulfur Dichloride ............... 31<br />

17.1.1.2.1.1.2.3.1.2 Variation 2: Reaction <strong>of</strong> Diaryl Ether with Sulfur Dication ................. 31<br />

17.1.1.2.1.1.2.4 Fragments C—C—S—C—C and O ............................................ 31<br />

17.1.1.2.1.1.2.4.1 Method 1: Reaction <strong>of</strong> Bis(chloroaryl) Sulfide with Oxygen Divalent<br />

Nucleophiles ............................................... 31<br />

17.1.1.2.1.1.2.4.2 Method 2: Reaction <strong>of</strong> Bis(dihydroxyphenyl) Sulfone with Oxidant ....... 32<br />

17.1.1.2.1.1.3 By Formation <strong>of</strong> One Heteroatom—Carbon Bond ............................ 32<br />

17.1.1.2.1.1.3.1 Fragment S—C—C—O—C—C ................................................ 32<br />

17.1.1.2.1.1.3.1.1 Method 1: Cyclization <strong>of</strong> a 1,2-S,O-Substituted Diaryl Ether ............. 32<br />

17.1.1.2.1.1.3.2 Fragment O—C—C—S—C—C ................................................ 33<br />

17.1.1.2.1.1.3.2.1 Method 1: Alkylative Cyclization <strong>of</strong> 2-(Arylsulfonyl)ethanone ............ 33<br />

17.1.1.2.1.1.3.2.2 Method 2: Cyclization <strong>of</strong> Diaryl Sulfides and Sulfoxides ................. 34<br />

17.1.1.2.1.2 By Annulation to the Heterocyclic Ring ..................................... 35<br />

17.1.1.2.1.2.1 Method 1: Annulation <strong>of</strong> Heterocycles ................................. 35<br />

17.1.1.2.1.2.2 Method 2: Annulation <strong>of</strong> Carbocycles .................................. 36<br />

17.1.1.2.2 Synthesis by Ring Transformation ........................................... 36<br />

17.1.1.2.2.1 Method 1: Ring Enlargement .......................................... 36<br />

17.1.1.2.2.2 Method 2: Formal Exchange <strong>of</strong> Ring Members with Retention <strong>of</strong> the Ring<br />

Size ....................................................... 38<br />

17.1.1.2.3 Aromatization ............................................................. 38<br />

17.1.1.2.3.1 Method 1: Elimination from 2,3-Dihydro-1,4-benzoxathiins ............. 38<br />

17.1.1.2.4 Synthesis by Substituent Modification ...................................... 39<br />

17.1.1.2.4.1 Substitution <strong>of</strong> Existing Substituents ........................................ 39<br />

17.1.1.2.4.1.1 Of Hydrogen ............................................................... 39<br />

17.1.1.2.4.1.1.1 Method 1: C-Formylation <strong>of</strong> 1,4-Benzoxathiins ......................... 39<br />

17.1.1.2.4.1.1.2 Method 2: Electrophilic Substitution <strong>of</strong> Phenoxathiin ................... 39<br />

17.1.1.2.4.1.2 Of Metals ........................................................... 42<br />

17.1.1.2.4.1.2.1 Method 1: Substitution Reactions Involving Organolithium Derivatives .. 42<br />

17.1.1.2.4.1.2.2 Method 2: Substitution Reactions Involving Transition-Metal Complexes . 45<br />

17.1.1.2.4.1.3 Of Carbon Functionalities .................................................. 45<br />

17.1.1.2.4.1.3.1 Method 1: Reactions Involving Rearrangement <strong>of</strong> Nitrogen onto an<br />

Annulated Ring Carbon ..................................... 45<br />

17.1.1.2.4.1.3.2 Method 2: Reactions Involving Decarboxylation at an Annulated<br />

Ring Carbon ............................................... 46

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