Tetrahedron

A mechanistic study of the ammonolysis of alkyl acetoacetates in water. Formation of 1, 5-dimethyl-2, 6, 9-triaza-bicyclo [3.3. 1] nonane-3, 7-dione as the main product

R Paredes, R Abonia, J Cadavid, R Moreno-Fuquen…

文献索引：Paredes, Rodrigo; Abonia, Rodrigo; Cadavid, John; Moreno-Fuquen, Rodolfo; Jaramillo, Alonso; Hormaza, Angelina; Ramirez, Alfonso; Kennedy, Allan Tetrahedron, 2002 , vol. 58, # 1 p. 55 - 60

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被引用次数: 3

摘要

We have presented evidence in favor of an enol mechanism to explain the rapid alkaline hydrolysis of ethyl acetoacetate in water and the first-order kinetics observed when a dilute equimolar (1.0×10 −4 M) solution of ester and HO − is allowed to react at room temperature. 1 The mechanism first involves the establishment of base catalyzed keto–enol equilibrium, via the enolate anion, between the ester and enols CH 3 C(OH)CHCO 2 Et and CH 3 COCHC(OH)OEt ...