Unsaturated ketones base-catalyzed hydration

Jarsjo J, Destouni G, Yaron B (1994) Retention and volatilization of kerosene Laboratory experiments on glacial and post glacial sods. J Contam Hydrol 17 167-185 Jarsjo J, Destouni G, Yaron B (1997) On the relation between viscosity and hydraulic conductivity values for volatile organic liquid mixtures in soils. J Contam Hydrol 25 113-127 Jensen JL, Hashtroudi H (1976) Base-catalyzed hydration of a, 3-unsaturated ketones. J Organic Chem 41 3299-3302... 

Mechanism of Base-Catalyzed Hydration of o ,/3-Unsaturated Aldehydes and Ketones... 

There also exists an acidregioselective condensation of the aldol type, namely the Mannich reaction (B. Reichert, 1959 H. Hellmann, 1960 see also p. 291f.). The condensation of secondary amines with aldehydes yields Immonium salts, which react with ketones to give 3-amino ketones (=Mannich bases). Ketones with two enolizable CHj-groupings may form 1,5-diamino-3-pentanones, but monosubstitution products can always be obtained in high yield. Unsymmetrical ketones react preferentially at the most highly substituted carbon atom. Sterical hindrance can reverse this regioselectivity. Thermal elimination of amines leads to the a,)3-unsaturated ketone. Another efficient pathway to vinyl ketones starts with the addition of terminal alkynes to immonium salts. On mercury(ll) catalyzed hydration the product is converted to the Mannich base (H. Smith, 1964). 

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See also in sourсe #XX -- [ ]

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