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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Indole ring expansion into quinolines with TMSCCl3/TMSCBr3.

Zhixin Wang1, Hanxiao Xu1, Xuanzhen Han1

  • 1Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, China. jinz@nju.edu.cn.

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Reactivity adaptation speciation explains how reactants form dynamic units for diverse chemical reactions. This study reveals C2-C3 insertion ring expansion of indole into quinoline and nucleophilic substitutions.

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Area of Science:

  • Organic Chemistry
  • Chemical Reactivity Theory

Background:

  • Understanding chemical reactivity is crucial for designing synthetic pathways.
  • Adaptation speciation offers a novel framework for analyzing reactant behavior in complex reactions.

Purpose of the Study:

  • To explore reactivity adaptation speciation using indole as a model system.
  • To investigate novel C2-C3 insertion ring expansion and nucleophilic substitution reactions.

Main Methods:

  • Utilized indole with TMSCCl3 and TMSCBr3 reagents.
  • Analyzed reaction products to elucidate reaction mechanisms.

Main Results:

  • Demonstrated C2-C3 insertion ring expansion of indole to quinoline.
  • Observed N1-H-TMS nucleophilic substitution and N1-H-CCl3 nucleophilic substitution pathways.
  • Characterized the formation of indole-TMSCCl3/TMSCBr3 adducts.

Conclusions:

  • Reactivity adaptation speciation provides a useful model for understanding complex organic reactions.
  • The study expands the known reactivity of indoles, offering new synthetic possibilities.