Hydrolysis of enamines

Hydrolysis of simple enamines appears to be very easy, and decomposition to the corresponding carbonyl compound and the secondary amine can be achieved readily for most enamines by adding water to them. Basicity as well as resonance may be considered important factors which, among other effects, will determine the rate of proton addition from water. Not less important is the question of where the proton will add, on nitrogen or on the 3-carbon atom. It is well known that carbon alkylation of enamines is mainly restricted to strongly electro-philic halides [1]. The use of weakly electrophilic halides, such as primary alkyl halides, leads to the very likely irreversib le formation of quaternary ammonium salts, in which the double bond is unreactive for further electrophilic attack, thus preventing the desired carbon alkylation.