Studies On The Synthesis Of α-Acetoxy Ketones

The thesis consists of two parts:The first part is a summation, which consists of three chapters. The first chapter mainly introduces the application of (diacetoxyiodo)benzene which is one of typical hypervalent iodine compounds in organic synthesis. The chapter is to summarize the progress of polyvalent iodine compounds in organic synthetic reaction such as oxidation, addition, substitution and rearrangement in recent ten years. The second chapter introduces the method for theα-acetoxylation of ketones using (diacetoxyiodo)benzene which was used instead of lead tetraacetate as the oxidation. The third chapter detailedly introduces the method for theα-acetoxylation of ketones using iodobenzene as a catalyst and 3-chloroperoxybenzoic acid as a terminal oxidant.The second part is our study on the improvement inα-acetoxylation of ketones. Our reaction was performed in good yield using 30% aqueous hydrogen peroxide and acetic anhydride which were used instead of 3-chloroperoxybenzoic acid as a terminal oxidant and iodobenzene as a catalyst. Sixteenα-acetoxy ketones were synthesized successfully. This synthetic procedure can be applied in theα-acetoxylation of aryl ketones and aliphatic ketones. Our method is more economical and faster and has a higher yield compared to the previous methods. All those mentioned compounds have been determined by ¹H NMR, ¹³C NMR, MS, EA and IR.