Jacobsen rearrangement

What is Jacobsen rearrangement?

The Jacobsen rearrangement is a chemical reaction that involves the treatment of polymethylbenzenes with concentrated sulfuric acid, H2SO4. This reaction results in the formation of rearranged polymethylbenzenesulfonic acids.

Jacobsen rearrangement
Jacobsen rearrangement

However, it is important to note that under the same conditions, halogenated polymethylbenzenes will undergo disproportionation instead.

References

  • Jacobsen, O. (1886), Ueber die Einwirkung von Schwefelsäure auf Durol und über das dritte Tetramethylbenzol. [On the effect of sulfuric acid on durol and on the third tetramethylbenzene.] Ber. Dtsch. Chem. Ges., 19: 1209-1217. https://doi.org/10.1002/cber.188601901274
  • Jacobsen, O. (1887), Ueber das Pentamethylbenzol und sein Verhalten gegen Schwefelsäure. [On pentamethylbenzene and its behavior against sulfuric acid.] Ber. Dtsch. Chem. Ges., 20: 896-902. https://doi.org/10.1002/cber.188702001205
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