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Basic properties and reactions of organosilicon compounds

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Friends who know EOC know that EOC is the abbreviation of organic chemistry. I am interested in organic elements and I am running the official account. Before, it was mainly related to fluorine chemistry. Recently, I had a little more understanding of silicon chemistry, and I was ready to plan a series. Silicon chemistry has rich and colorful connotations. Its unique reactions are all due to its electronegativity, steric hindrance and corresponding atomic orbital. The author thinks that its most important properties are five coordination anions, α - silicon effect and β - silicon effect. EOC will sort out the contents of organosilicon chemistry systematically, and then carry on the serialization according to the contents, such as organic reaction in which silicon anion participates as nucleophile, application of silicon cation as Lewis acid in catalysis, activation of Si-H bond, C-H bond silylation, application of silicon-containing compounds in coupling reaction, etc. Each part can be further refined. For example, C-H bond silylation can be divided into metal catalysis, non-metal catalysis silylation and so on. This part has been written and will be published in serial form this week.


Organosilicon chemistry is an important part of the organic chemistry of elements. Silicon is located in the fourth group of the third period of the periodic table of elements, and its properties are between nonmetal and metal. Organosilicon compounds are often used as hydroxyl protecting groups in organic synthesis, such as trimethylsilyl, tert butyl Dimethylsilyl, phenyldimethylsilyl, etc. In addition, organosilicon polymers are widely used.


Compared with carbon, silicon has less electronegativity, so it is easy to be attacked by nucleophiles. It can be seen from some bond length and bond energy data in the figure below that the effect between Si and F is very strong. TBAF (tetrabutylammonium fluoride) is often used to protect the hydroxyl group from desilication, and fluoride anion is often used as the activator of organosilicon reagent; the effect between Si and O is also very strong, and silicon ether polymer is widely used in material science; c-Si bond carbon is a negative center, which can react with various electrophilic reagents Should, such as the hyama coupling reaction.

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