HYDROLYSIS OF FLUOROALKYL-CONTAINING β-AMINOVINYL KETONES

Article abstract of DOI:10.1007/BF00957999

The kinetics of hydrolysis of fluoroalkyl-containing β-aminovinyl ketones R1C(O)CHC(NHR3)R2, in which the substituents CF3 and HCF2CF2 are in the ketone (R1) or enamine parts of the molecule (R2), was studied.In acid (pH < 5) and alkaline (pH > 10) media, they hydrolyze with the formation of the corresponding amines and β-diketones.In an alkaline medium, the β-diketones undergo cleavage to fluorinated acids and methyl ketones.The rate constants of hydrolysis in an acid medium change within a range of four orders, depensdng on the nature of the substituents.The presence of a fluoroalkyl group at the enamine reaction center increases the hydrolysis rate.In an alkaline medium, the rate constants vary within one order.