Related Experiment Video
Updated: May 15, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Direct synthesis of organothianthrenium salts under ball milling conditions
Pan Gao1, Ya Yang1, Xinting Fan1
1School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China. gaopan@yzu.edu.cn.
Abstract:
We report a solvent-free mechanochemical synthesis of organothianthrenium salts via direct C-H thianthrenation under ball-milling conditions. This approach eliminates the need for hazardous reagents, inert gas protection, and elaborate reaction setups while offering high efficiency and excellent functional group tolerance. The optimized conditions provide aryl and alkyl thianthrenium salts in high yields, demonstrating broad substrate scope and scalability. Comparative analysis highlights the method's environmental benefits, significantly reducing reaction time and waste generation. This mechanochemical strategy provides a sustainable and practical alternative for synthesizing valuable thianthrenium salts with diverse applications in synthetic chemistry.
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Nitriles
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Esters to Alcohols: Grignard Reaction
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...

