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[Chemical Knowledge]：Commonly used sulfonation reagents and their differences

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Commonly Used Sulfonating Reagents and Their Distinguishing
Sulfonating reagents are a class of commonly used organic synthesis reagents having a sulfonating group capable of introducing a sulfonate ester functional group into an organic compound. Sulfonating reagents have attracted the attention of researchers because of their importance and wide application in synthesis. This article will introduce several commonly used sulfonation reagents and their differences to help readers choose suitable reagents for experiments.

1. disulfonate sulfonation reagent

disulfonate sulfonation reagent is the most commonly used sulfonation reagent, its general formula is R-SO2-OR '. These reagents have high sulfonation reactivity and good steric hindrance effect, and can be used for the intervention reaction of sulfonate functional groups. In addition, this kind of reagent has good stability, is not easy to decompose, is easy to prepare, and the price is relatively low. Common disulfonate reagents include methyl methanesulfonate, p-toluenesulfonate, etc.

2. sulfinate sulfonating reagent

sulfinate sulfonating reagent is a kind of reagent with active sulfonate functional group, its general formula is R-SO2-SR '. Compared with disulfonate reagents, sulfinate reagents have higher activity, but poor stability and easy decomposition. Such reagents have good selectivity for some reactions. Common sulfinate reagents include benzene sulfinate, p-toluene sulfonic acid silicon ester, etc.

3. sulfonyl chloride sulfonation reagent

sulfonyl chloride sulfonation reagent is a kind of high activity sulfonation reagent, its general formula is R-SO2-Cl. The sulfonyl chloride reagent has extremely high reactivity, but it has poor stability and is easy to hydrolyze, so it needs attention when using it. Compared to disulfonate and sulfinate reagents, sulfonyl chloride reagents react more readily and in higher yields for less reactive substrates. Common sulfonyl chloride reagents are p-toluenesulfonyl chloride, tert-butyl sulfonyl chloride, etc.

4. sulfinyl chloride sulfonation reagent

sulfinyl chloride sulfonation reagent is a kind of reagent with high activity, and its general formula is R-SO2-OSO2R '. This kind of reagent activity is higher, but it is easy to decompose. The sulfinyl chloride reagent has good activity and selectivity for the sulfonation reaction of olefins and aromatic hydrocarbons. Common sulfinyl chloride reagents are p-toluene sulfinyl chloride, tert-butyl sulfinyl chloride, etc.

summary: This article introduces several commonly used sulfonating reagents and their differences. Different sulfonating reagents have different activity and stability in the reaction, and the suitable reaction conditions are also different. When selecting a sulfonation reagent, the experimental requirements, the reaction substrate, and the nature of the reagent need to be considered. It is hoped that through the introduction of this paper, readers can better select and use sulfonation reagents to improve the effect of experimental research.