Related Experiment Video
Updated: Oct 29, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Selective oxidative intermolecular carbosulphenylation of aryl alkenes with thiols and nucleophiles via a
Yuna Wang1, Zaojuan Qi2, Yanning Niu3
1State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China. ebenassi3@gmail.com boqian@licp.cas.cn and Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. China. hfeng@nwnu.edu.cn.
Abstract:
A periodate lithium-oxidized difunctionalisation of aryl alkenes with thiols and electron-rich aromatics was achieved, selectively affording more than thirty carbosulphenylated products. Both experiments and quantum chemical calculations demonstrated the radical-polar nature of the processes, and that 1,2-dithioethane and thiiranium ions might play the role of intermediates.
More Related Videos
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Related Concept Videos
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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...