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

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

Introduction<br />

S. M. Weinreb and Y. R. Mahajan<br />

Introduction ............................................................ 1<br />

17.1 Product Class 1: Six-Membered Hetarenes with Two Unlike Heteroatoms<br />

17.1.1 Product Subclass 1: Two Unlike Oxygen, Sulfur, Selenium,<br />

or Tellurium Atoms<br />

S. Yamazaki and K. Yamamoto<br />

17.1.1 Product Subclass 1: Two Unlike Oxygen, Sulfur, Selenium,<br />

or Tellurium Atoms ....................................................... 19<br />

17.1.1.1 1,4-Oxathiins .............................................................. 21<br />

17.1.1.1.1 Synthesis by Ring-Closure Reactions ........................................ 21<br />

17.1.1.1.1.1 Method 1: Reaction <strong>of</strong> Sulfur Dichloride with Divinyl Ether .............. 21<br />

17.1.1.1.2 Synthesis by Ring Transformation ........................................... 22<br />

17.1.1.1.2.1 Method 1: Rearrangement <strong>of</strong> 1,3-Oxathiolanes ......................... 22<br />

17.1.1.1.3 Aromatization ............................................................. 22<br />

17.1.1.1.3.1 Method 1: Dehydrochlorination ....................................... 22<br />

17.1.1.1.3.2 Method 2: Pummerer Reaction ........................................ 22<br />

17.1.1.1.4 Synthesis by Substituent Modification ...................................... 23<br />

17.1.1.1.4.1 Addition <strong>of</strong> Heteroatoms .................................................. 23<br />

17.1.1.1.4.1.1 Method 1: Oxidation <strong>of</strong> a Ring Sulfur .................................. 23<br />

17.1.1.1.4.2 Modification <strong>of</strong> Substituents ............................................... 24<br />

17.1.1.1.4.2.1 Method 1: Condensation Reaction <strong>of</strong> the Carboxy Group with Aniline<br />

Derivatives ................................................ 24<br />

17.1.1.2 Annulated 1,4-Oxathiins ................................................... 24<br />

17.1.1.2.1 Synthesis by Ring-Closure Reactions ........................................ 24<br />

17.1.1.2.1.1 By Annulation to an Arene ................................................. 24<br />

17.1.1.2.1.1.1 By Formation <strong>of</strong> Three Heteroatom—Carbon Bonds .......................... 24<br />

17.1.1.2.1.1.1.1 Fragments O—C—C, C—C, and S ............................................ 24<br />

17.1.1.2.1.1.1.1.1 Method 1: Reaction <strong>of</strong> Monoimines with Phosphorus Pentasulfide ....... 24<br />

17.1.1.2.1.1.2 By Formation <strong>of</strong> Two Heteroatom—Carbon Bonds ........................... 25<br />

17.1.1.2.1.1.2.1 Fragments S—C—C—O and C—C ............................................ 25<br />

17.1.1.2.1.1.2.1.1 Method 1: Reactions Involving Nucleophilic Sulfur and Oxygen .......... 25<br />

17.1.1.2.1.1.2.1.2 Method 2: Cycloaddition Reactions .................................... 27<br />

17.1.1.2.1.1.2.2 Fragments S—C—C and O—C—C ............................................ 28

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