Preparation And Application Of Carbonyl Selenides In Organic Synthesis

This dissertation consists of two parts.In the first part, we summarize the synthesis of selenol esters and the advance in the applications of Selenol esters as important reagents and intermediates in organic synthesis. Selenol esters have been employed as precursors of acyl radicals for several kinds of intermolecular and intramolecular free radical reactions. The mechanism of these typical free radical reactions are introduced and discussed.In the second part, we report a convenient synthesis of diacyl diselenides and develop the new routes for the preparation of ferrocenoyl selenol esters. The mechanisms of these reactions are proposed and discussed.In the first chapter, we prepare the arylselenoamides which is the starting material for the subsequent reactions.In the second chapter, we synthesize a series of diacyl diselenides by the reaction of arylselenoamides with acyl chlorides using chloroform as solvent. The mechanism of this reaction is proposed and discussed. We provide a new convenient method for the synthesis of diacyl diselenides.In the last chapter, we introduce the synthesis and extensive applications of ferrocene and ferrocene derivatives. A series of ferrocenoyl selenol esters were synthesized, using arylselenoamides with ferrocenoyl halides and organic halides, under liquid-liquid phase-transfer conditions. We find two routes for the preparation: the one pot synthesis and the two-step synthesis. We also discuss the mechanism of these reactions when using different kinds of organic halides.This is the first report of the synthesis of ferrocenoyl selenol esters under liquid-liquid phase-transfer conditions. We synthesize a series of new compounds, and provide new efficient methods for the synthesis of ferrocenoyl selenol esters.