Schmidt-Rutz reaction

What is Schmidt-Rutz reaction?

The Schmidt-Rutz reaction is a method for synthesizing nitroolefins that was first reported by Schmidt and Rutz in 1928. The process involves treating acetates of α-nitro-alcohols with sodium bicarbonate NaHCO3, and it is also known as the Schmidt-Rutz degradation.

Schmidt-Rutz reaction - general reaction scheme - Schmidt-Rutz degradation
Schmidt-Rutz reaction

R, R’ = H, alkyl, aryl (see list of acronyms)

While the reaction is most suitable for α-nitro esters with one proton at the α-carbon bonded to the nitro group, it can still form 1-nitro-olefins despite this restriction. The Schmidt-Rutz reaction is applicable to substrates without any other base-labile functional groups and typically yields nitro-olefins in good amounts.

The best yields are obtained from esters of nitro-alcohols with nine or more than nine carbon atoms. The reaction can also use mild bases such as potassium bicarbonate, sodium carbonate, and sodium acetate instead of sodium bicarbonate. Nitro-olefins produced by the Schmidt-Rutz reaction can be reduced to amines, making this reaction a useful method for producing amines with a specific structure that is free of isomers.

The Schmidt-Rutz reaction has found wide application in carbohydrate chemistry, thanks to the good crystalline capability of nitro carbohydrate acetates that can easily crystallize even in the presence of a large number of other carbohydrate acetates.

References

  • Schmidt, E.; Rutz, G. and Trenel, M., Ber., 1928, 61, 472
  • Schmidt, E. and Rutz, G., Ber., 1928, 61, 2142
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