ter Meer reaction

What is ter Meer reaction?

The ter Meer reaction, also known as the ter Meer synthesis, was first reported by ter Meer in 1876. ter Meer reaction involves the halogenation of mono-nitroalkanes and displacement of the halide by nitrite under basic conditions, resulting in the synthesis of terminal gem-dinitro compounds.

ter Meer reaction - general reaction scheme
ter Meer reaction

Some examples of compounds synthesized using ter Meer reaction include the potassium salt of dinitromethane, 2,2-dinitroethanol, 1,1-dinitropropane, and 1,1,4,4-tetranitrobutane.

However, the synthesis often fails to produce internal gemdinitroalkanes such as 2,2-dinitropropane. Additionally, the formed terminal gem-dinitro compounds may undergo other reactions such as a Michael condensation or Mannich reaction, resulting in the formation of other side products. It is worth noting that even though the reaction occurs under basic conditions, an excess amount of strong base may inhibit its progress.

References

ter Meer, E. (1876), Ueber Dinitroverbindungen der Fettreihe. Justus Liebigs Ann. Chem., 181: 1-22. https://doi.org/10.1002/jlac.18761810102

Shares