Related Experiment Video
Updated: Feb 13, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study
Lijun Fu1, Xueli Mu1, Baiqing Li2
1Institute of Theoretical Chemistry, School of Chemistry and Chemical Engineering and Key Laboratory of Colloid and Interface Chemistry (Ministry of Education), Shandong University, Jinan, Shandong, 250100, People's Republic of China.
Abstract:
A new method for the syn-dichlorination of alkenes at room temperature has been proposed by Denmark et al. The method uses diselenide (PhSeSePh) as the precatalyst, benzyltriethylammonium chloride (BnEt3NCl) as the source of chlorine, and an N-fluoropyridinium salt as the oxidant to recover the catalyst. This approach has achieved exquisite diastereocontrol on a number of alkene substrates. In this paper, we report the results of DFT calculations we performed to study the mechanism of this reaction. We were able to identify a reasonable reaction path, including the intermediate and transition-state structures. The results also indicate that PhSeCl3, rather than PhSeCl, is the active catalyst.
More Related Videos
12:08Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
Published on: June 24, 2022
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Acid-Catalyzed Hydration of Alkenes
Reaction Mechanisms
For instance, the decomposition of ozone appears to follow a mechanism with two steps:
Acid-Catalyzed Dehydration of Alcohols to Alkenes
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction