Abstract
This chapter presents reaction of enamines with various compounds. It explains that certain ketones react reversibly with secondary amines to give enamines. By removal of water, the equilibrium can be driven to the right, and the enamine can be isolated. The β-position of enamines is highly nucleophilic and may react with alkyl halides, acyl chlorides or anhydrides, or with Michael addition substrates to give carbon–carbon bonds. The preparation of enamines of unsubstituted cyclic ketones is convenient and unambiguous. Moreover, such enamines have found wide application as means of chain extension or ring formation. In the acylation of enamines, the weakly basic acylated enamine does not absorb the acid formed. In that procedure, the chloroform and aqueous acid layers are separated, and the chloroform layer is washed twice with 100-ml portions of water. Further, β-propiolactone is subject to attack by enolate ions to give propionic acid derivatives of ketones. It may likewise react with nucleophilic enamines to give carboxyethylation according to the reactions.
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