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The Grob fragmentation of -halo-a-amino acids in aqueous solution has been studied, being first order in TV-halo-a-amino acid and pH-independent. The substituents on the C2 and N atoms strongly affect the reaction rate. Structure reactivity correlations for C2 substituents provide * values of -3.9 and -4.1 for N-Cl and -Br compounds, respectively. The same correlations for N substituents lead to * values of -2.1 and -1.9 for -Cl and -Br compounds. The transition state (TS) can be generally described as product-like, its structure and characteristics being significantly affected by the substituents on the C2 and on the N atoms. In conclusion, the reaction is a DEDN concerted and slightly nonsynchronous two-stage process.

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