醛(酮)缩合反应.ppt

Review of Chapter 3 Email: mengge@ Tel:o),m) :8080/web/mengge April, 17, 24, 27,2012 Acylation Methods Acylation on O: Esters Acylation on N: Amides Acylation on C: Ketones or aldehydes F-C Hoesch Formylation Gattermann (Special Hoesch) Vilsmeier-Haack Reimer-Tiemann Gattermann reaction The Gattermann reaction refers to a reaction of hydrocyanic acid with an aromatic compound, in this case benzene, under catalysis with Friedel-Crafts catalyst (aluminum chloride). The reaction is similar to the Friedel-Crafts reaction. Vilsmeier-Haack reaction The Vilsmeier-Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted amide with phosphorus oxychloride and an electron-rich arene to produce an aryl aldehyde or ketone. The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion, also called the Vilsmeier reagent. The initial product is an iminium ion, which is hydrolyzed to the corresponding aromatic ketone or aldehyde during workup. Reimer-Tiemann reaction The Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols. salicylaldehyde Chloroform reacts with strong base to form dichlorocarbene, which will react in the ortho-position of the phenate to give the dichloromethyl substituted phenol. After basic hydrolysis, the product is formed. Synthesis of aromatic aldehydes Other Formylation Methods: Duff reaction Functional group transformation Sommelet reaction Kr?hnke aldehyde synthesis reaction Oxidation (Chapter 6) Swern oxidation PCC oxidation CAN SeO2 Etard reaction monooxidation Reduction (Chapter 7) From carboxylate derivatives via metal hydride reduction Rosenmund reduction 第四章 缩合反应 Chapter 4 Condensation Reaction Intermolecular and intramolecular Intermolecular：When two separate molecules react, the condensation is termed intermolecular. A simple example is the condensation of two amin