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Three critical pathways are discovered, i.e., S-N bond cleavage, Cl-substitution onto aniline-N, and the following rearrangement to lose -SO2- group, among which Cl-substitution is the key step due to its lowest free energy barrier. Heterocycles impact the reaction rate by affecting the electronic density of aniline group. In general, the more electron-donating the heterocycle is, the more readily sulfonamides to be chlorinated.A method based on gas chromatography coupled with electron ionization mass spectrometry employing N,O-bis(trim
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