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Updated: Jun 20, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Experimental and theoretical studies on some energetic functionalized trimethylamine derivatives

Thomas M Klapötke1, Burkhard Krumm, Matthias Scherr

  • 1Department of Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München, Germany. tmk@cup.lmu.de

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 22, 2009
PubMed
Summary

Researchers synthesized and studied energetic compounds derived from tris(chloromethyl)amine. These compounds feature planar nitrogen-carbon units and reactive substituents, explained by multiple hyperconjugation.

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
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