Preparation Of Bisorganozinc Halides And Their Reaction With Acyl Chlorides

A considerable organic molecular have multi-functional group, particularly in drug molecular and natural product. The synthesis of this molecular will take a very long step. Therefore, how to shorten the synthesis steps to reduce the cost of organic synthesis is an important research subject.The spiroketal ring system exists in a wide range of natural products. Currently most of the method for the synthesis of spiroketal commonly has very long steps. In this thesis we designed a new method to synthesize the spiroketal units by use of bisorganozinc reagents. The important steps are the preparation of bisorganozinc and its reaction with aldehyde. Because there are many articles about organozinc reagents react with aldehyde, we investigated the preparation of bisorganozinc reagents and its reactions.This thesis includes three chapters.Chapter One: The development of organozinc halides in organic synthesis.In this section, the development, preparation and application of organozincs, especially the functional organozincs, are reviewed in details.Chapter Two: Bisorganozinc reagents and their reactions with acyl chlorides.As a preliminary work we prepared bisorganozinc halides directly from diiodide and zinc powder, and investigated their reaction with acyl chloride to give diketone, the reaction mechanism also proposed on the basis of experiments and the literatures. Fourteen products were synthesized by this procedure.Chapter Three: Functional bisorganozinc reagents and their reactions with acyl chlorides.We firstly prepared the functional bisorganozinc reagents and investigated their reactions with acyl chlorides. The reaction give functional diketone in moderate yield.