Studies On The Synthesis Of The Trifluoromethylated Compounds And The Reduction Of The Dinitro Compounds Containing An Ether Or Ester Linkage

The field of organofluoro chemistry has grown tremendously in recent years, and fluoro-containing chemicals have permeated nearly every aspect of our daily lives. Fluorine is the element of extremes, and many fluorinated organic compounds exhibit extreme and sometimes even bizarre properties, so there have been considerable in-depth research and development of organofluoro chemistry and chemicals in many high-end technology, bulk industrial projects, pesticides and pharmaceuticals.This paper introduces the synthesis of the compounds containing trifluoromethyl that use the(trifluoromethyl)trimethylsilane as the fluorine-containing building block and cesium fluoride as an initiator. Then reduction of the two nitro group containing an ether bond by the secondary and tertiary alcohols were carried out in a series of studies. The work of this thesis is divided into two parts.In part one: We studied the trifluoromethylation reaction of p-nitroacetophenone as the substrate and with the(trifluoromethyl)trimethylsilane as the fluorination agent. We investigated the influence of this reaction in different conditions such as solvents, initiators, temperature, time and so on. We determine the optimal conditions of this reaction: the cesium fluoride as an initiator, ethylene glycol dimethyl ether as a solvent at room temperature to achieve a good result of this reaction. Then we use some different aldehydes as the substrate, especially the natural camphor ring-breaking derivatives including diacylchloride, dimethyl formate and dialdehyde for a series of reactions with(trifluoromethyl)trimethylsilane.In part two: We use the trifluoromethylated compounds synthesized in part one, the tertiary alcohol precusor 1,1,1-trifluoro-2-(4-nitrophenyl)-2-trimethylsilyloxypropane to react with the p-nitrobenzoyl chloride to generate the dinitro compound. Another tertiary alcohol 1,1,1-trifluoro-2-(4-nitrophenyl)-2-propanol was used to reacted with 1-fluoro-4-nitrobenzene to obtain the dinitro compound, and comparatively, a primary alcohol 1-(4-nitrophenyl) ethanol was reacted with the p-nitrophenol to generate the dinitro compound and so on. We use the five different dinitro compounds which we had synthesied were reduced by hydrazine hydratein catalyzed by Pd/C. It was found that the reduction of tertiary alcohol derived dinitro compounds differs considerably from that of primary alcohol derived dinitro compound. These two types reduction were investigated and the possible mechanisms were put forward.