The Research On Ruthenium(Ⅱ)-Catalyzed Cyclopropane Reaction In The Sunlight And The Cyclopropane Reaction Induced By The Ultraviolet Ray

Cyclopropyl compounds are a class of very important organic compounds, which have a extensive range of applications in medicine, pesticide, biological chemistry and other industries for its perfect biological activity and selectivity; At the same time, three-membered ring structure was widely existed in the molecular structure of various natural products. Thus, the development of efficient synthetic methods for cyclopropyl compounds synthesis is highly desired and of great importance for organic synthesis. The research in this job is also an important part of chemical synthetic methodology.The way to synthesize cyclopropyl compounds was study extensively before, such as Ruthenium-catalyzed cyclopropane reaction though aza cabbeen, Samarium-catalyzed Simmons-Smith reaction and so on. My research is mainly about the Ru (Ⅱ)-catalyzed cyclopropane reaction in the presence of sunlight, which prevents a new method to produce cyclopropyl compounds.My research job is composed of the following sections,Part Ⅰ:Based on the widely review relevant literatures, the esperimental idea and concrete experimental program were proposed.Part Ⅱ:The optimization of the Ru (Ⅱ)-catalyzed cyclopropane reaction was carried out carefully. The different wavelengths, ratio of substrate, solvent effect, the amount of organic amine additives, the amount of catalysts, and a series of controlled trials were examined step by step, and then the optimized reaction conditions were confirmed.Part Ⅲ:The different substrates with arenes were studied after the optimized reaction conditions. Electron effect, steric effect, and substituent effect were examined. And the relevant law was summed up.Part Ⅳ:The possible mechanism was discussed and supposed based on the experimental results.Part Ⅴ：Upon the results of the experience, the cyclopropane reaction was extended to the 185 nm ultraviolet ray condition.A new synthetic method for cyclopropyl derivatives was developed during this research, which proceeds via the cyclopropane reaction of geminal dibromo compounds and electron-deficient alkene substrate under the catalysis of ruthenium (Ⅱ) in the sunlight, or under the condition of ultraviolet ray. The two mechanisms of these reactions are different from any other literature reported cases.