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Emde degradation
The Emde degradation (also called Emde-reaction or Emde-reduction) is a method for the reduction of a quaternary ammonium cation to a tertiary amine with sodium amalgam:

This organic reaction was first described in 1909 by the German chemist Hermann Emde. It was for a long time of great importance in structure elucidation of many alkaloids, for example that of ephedrine.
Alternative reducing agents exist for this reaction; for instance, lithium aluminium hydride.
References
References
- (1909). "Spaltung quartärer Ammoniumsalze durch nascierenden Wasserstoff". [[Ber. Dtsch. Chem. Ges.]].
- (1989). "Lexikon bedeutender Chemiker". VEB Bibliographisches Institut Leipzig.
- (2001). "March's Advanced Organic Chemistry". Wiley.
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