有机合成讲义SN2.pptVIP

III. Halogen nucleophiles A. Attack at an alkyl carbon 1. Halide exchange Used for the preparations of iodides and fluorides Configuration retains 2. Formation of alkyl halides from esters of sulfuric and sulfonic acids 3. Formation of alkyl halides from alcohol Other useful halogenating agents for alcohols: Et2NSF3(DAST) for fluorination of alcohols Selective halogenation of NBS and NCS Only effects on allylic or benzylic alcohols 4. Formation of alkyl halides from ethers 5. Cleavage of carboxylic esters with lithium iodide 6. Conversion of amines to halides B. Attack an acyl carbon Form