Emde degradation amines

The reductive cleavage of quaternary ammonium salts to give a tertiary amine and a hydrocarbon by reaction with sodium amalgam in hydroxylic solvents is called the Emde degradation. However, saturated hydrocarbons are not cleaved under these conditions. Grovenstein suggested that the reason for this unreactivity is due to the fact that the sodium reacts with the alcohol much faster than with the ammonium salts. However, by operating in dioxane or dioxane-alcohol mixtures, the dealkylation reaction could be accomplished. The products of the decomposition of either tetramethylammonium chloride or bromide are methane, ethylene, trimethylamine, and dimethylethylamine. 

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