Mechanism of base-catalyzed cyclization of ethyl N-(substituted aminocarbonyl) glycinates

J Mindl, V Štěrba

文献索引：Mindl, Jaromir; Sterba, Vojeslav Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 1 p. 156 - 161

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被引用次数: 2

摘要

Abstract The cyclization rate constants have been measured of substituted ethyl N- (phenylaminocarbonyl)-, N-(alkylaminocarbonyl)-, and N-(phenylaminothiocarbonyl) glycinates RNHCXNHCH 2 CO 2. C 2 H 5 (X= O, S). Logarithms of these constants increase with decreasing basicity of the amines down to the value of pK a (RNH 2)= 5.5. The rate- limiting step of the reaction is formation of the tetrahedral intermediate. With ethyl N-( ...