Victor Meyer reaction

What is Victor Meyer reaction?

The Victor Meyer reaction, which involves the formation of a nitroalkane from the reaction between an alkyl halide and silver nitrite AgNO2, was first reported by Victor Meyer et al. in 1872. Victor Meyer reaction is typically carried out in petroleum ether or dialkyl ether at temperatures ranging from 80 to 110 ºC, and results in a mixture of nitroalkane and alkylnitrite due to the bidenate nature of nitrite.

Victor Meyer reaction - general reaction scheme
Victor Meyer reaction

The ratio of nitroalkane and alkylnitrite varies depending on the nature of the alkyl halide and metal nitrite. The yields of nitroalkanes decrease progressively when silver nitrite reacts with primary, secondary, and tertiary halide, while the yields of corresponding alkyl nitrite increase in the inverse order. This change in product ratio may be due to both steric and electronic effects. Although the reaction’s workup process is tedious, and its yield is relatively low, it is still the most convenient method for preparing the homologues of primary nitroalkanes higher than 1-nitropropane.

Victor Meyer reaction has been modified to produce pure nitroalkane by reacting alkyl halide with an excess amount of silver nitrite and washing the reaction mixture with concentrated sulfuric acid or phosphoric acid to remove alkyl nitrite before distillation. Sodium nitrite NaNO2 and potassium nitrite KNO2 have also been used to prepare nitroalkanes from alkyl halides under various conditions. It is noteworthy that this nucleophilic substitution undergoes via a transition state of both SN1 and SN2 characters, which vary with the structure of halide, rather than being the sum of two simultaneously occurring processes.

References

  • Meyer, V.; Stuber, O.; Rilliet, A., and Chojnacki, C., Ann., 1872, 171, 1
  • Meyer, V. and Stuber, O., Ber., 1872, 5, 203
  • Meyer, V. and Stuber, O., Ber., 1872, 5, 399
  • Meyer, V. and Rilliet, A., Ber., 1872, 5, 1032
  • Meyer, V. and Chojnacki, C., Ber., 1872, 5, 1037
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