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シリル基媒介によるスルファモイル塩化物の活性化により,アルケンのアリファティック・スルフォナミドに直接アクセスできます.

  • 0University of Oxford , Chemistry Research Laboratory , 12 Mansfield Road , Oxford OX1 3TA , United Kingdom.

まとめ

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Preparation and Reactions of Sulfides 02:26

5.6K

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.

Asymmetrical sulfides can be synthesized by treating thiols with an alkyl halide and a...

Radical Substitution: Allylic Bromination 01:27

6.3K

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents 01:27

9.7K

In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...

Conversion of Alcohols to Alkyl Halides 02:48

8.2K

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...

Radical Reactivity: Nucleophilic Radicals 01:16

2.6K

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...

Radical Anti-Markovnikov Addition to Alkenes: Overview 01:25

3.9K

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

The observed regioselectivity can be explained based on the radical stability and steric effect. From the radical stability perspective, adding hydrogen bromide in the presence of peroxide directs the bromine radical at the less substituted carbon via a more stable tertiary radical intermediate. Similarly, in the steric framework, the...