Orden del obsidiano

The reaction of Eschweiler-Clarke , also called methylation of Eschweiler-Clarke , is a reducing reaction of Amination by which a primary or secondary amine is methylated, by formic formaldehyde and acid excess. These conditions do not produce ammonium salts.

Mechanism

The reaction starts with the formation of a Imine with the Formaldéhyde. Then the formic Acid reduces the imine in secondary amine. The driving force of the reaction comes from the release of Carbon dioxide. The formation of the tertiary amine follows the same process but is slower because of the difficulty of formation of the cation Iminium.

This mechanism excludes the passage by an ion ammonium because of the secondary intermediary imine. That thus prohibits the Racémisation chiral amines .

References

  • Eschweiler, W.; Ber. 1905 , 38 , 880.
  • Clarke, H.T.; Gillespie, H.B.; Weisshaus, S.Z.; Newspaper off the American Chemical Society|J. amndt Chem. Plowshare 1933 , 55 , 4571.
  • Moore, Org. React. 1949 , 5 , 301.
  • Farkas, E.; Sunman, C.J.; J. Org. Chem. 1985 , 50 , 1110.

See too

  • Amination reducing
  • Reaction of Leuckart-Wallach

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