Synthesis and reactivity studies of the α, α- dihalo-α'/β-acetoxyketones

Abstract

Chapter 1 describes the essential background on the synthesis of α, α-dihalocarbonyl moieties and their use as building blocks for the development of novel synthetic transformations in organic synthesis. These key building blocks have been employed for several traditional transformations such as oxidations, reductions, C-C bond formations, as well as in some of the non-classical reactions. Chapter 2 describes a highly regioselective and efficient synthesis of a new class of gemdihaloketones, i.e., α, α- dihalo-α'/β-acetoxyketones from terminal propargylic acetates and Nhalosuccinimides under mild conditions. This metal free transformation is very general and shown compatibility for divergent structural types of propargylic acetates with terminal alkyne unit, such as tertiary-(aryl-aryl; aryl-alkyl; alkyl-alkyl), secondary-(aryl; alkyl) and primary acetates. The process involves an acetate directed, dihalo-hydration pathway.