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Trichloroisocyanuric acid in 98% sulfuric acid: A superelectrophilic medium for chlorination of deactivated arenes

Paper ID Volume ID Publish Year Pages File Format Full-Text
41576 45893 2011 6 PDF Available
Title
Trichloroisocyanuric acid in 98% sulfuric acid: A superelectrophilic medium for chlorination of deactivated arenes
Abstract

Trichloroisocyanuric acid (TCCA) reacts with arenes and its reactivity is highly affected by the acid strength of the reaction medium. Deactivated arenes are efficiently chlorinated by TCCA in H2SO4. Our results, along with DFT calculations and 13C NMR spectrometry suggest the formation of a monoprotonated TCCA superelectrophile as the reactive species that can efficiently transfer electrophilic Cl+ to even very weak nucleophiles, such as m-dinitrobenzene.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (11 K)Download as PowerPoint slideHighlights► TCCA is safe, stable, and easily available reagent with high atom economy. ► TCCA is monoprotonated by 98% H2SO4. ► DFT calculations support the formation of a superelectrophilic species. ► TCCA in 98% H2SO4 can chlorinate arenes, even strongly deactivated substrates. ► The reactivity of TCCA is regulated by the acid strength of the medium.

Keywords
Trichloroisocyanuric acid; DFT Calculations; Arenes; Superelectrophilic species; Aromatic chlorination
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Trichloroisocyanuric acid in 98% sulfuric acid: A superelectrophilic medium for chlorination of deactivated arenes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 401, Issues 1–2, 15 July 2011, Pages 176–181
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us