硫胺N-功能化与N-甲硫胺
Žan Testen1, Črtomir Podlipnik1, Marjan Jereb1
1University of Ljubljana, Faculty of Chemistry and Chemical Technology, Večna pot 113, 1000 Ljubljana, Slovenia.
The Journal of organic chemistry
|October 29, 2025
概括
一种新的无金属方法有效地使用N-fluorobenzenesulfonamide转化硫胺. 这种可扩展的工艺可以从各种基板中高效率地产生有价值的产品.
科学领域:
- 有机化学 有机化学
- 合成方法论 合成方法论
背景情况:
- 硫胺是多功能合成中间体.
- 开发高效和温和的合成路径至关重要.
研究的目的:
- 提出一种新的,简单的,可扩展的硫胺功能化的方法.
- 探索合成产品的范围和反应性.
主要方法:
- N-H-硫胺与N-化硫胺的反应.
- 在乙烯酸乙酸中使用2,2,6,6-四甲基 (TMP) 作为基.
- 使用NMR,X射线晶体学和DFT计算进行产品表征.
主要成果:
- 实现了广泛的硫胺衍生物的高产率 (>75%).
- 证明了基质与氨基,化物,和氨基酸的兼容性.
- 成功扩展到克数量的过程一致性.
结论:
- 开发的方法为硫胺化学提供了一种方便,温和和无金属的方法.
- 合成的产品表现出稳定性,并作为进一步转换的多功能基质.
- DFT计算提供了对反应机制和能量概况的见解.
相关概念视频
Electrophilic Aromatic Substitution: Sulfonation of Benzene
7.8K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
7.8K
Amines to Sulfonamides: The Hinsberg Test
4.4K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.4K
Preparation and Reactions of Sulfides
5.7K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.7K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
7.3K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.3K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.6K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.6K
Electrophilic Aromatic Substitution: Nitration of Benzene
8.2K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
8.2K
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