Abstract
Reactions of acyl iodides RCOI (R=Me, Ph) with glycine, β-alanine, and γ-aminobutyric acid were investigated. The reaction proceeded easily at room temperature without solvent involving both functional groups H2N and COOH. The prevalence of one of the reaction directions depends on the acidity of the amino acid. The more acidic glycine (pКa 2.4) reacts with RCOI affording mainly N-acylated product, whereas β-alanine (pКa 3.60) and especially γ-aminobutyric acid (pКa 4.06) are predominantly involved into exchange iodination furnishing the corresponding aminoacyl iodides.
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