Synthesis and Physicochemical Properties of C-Borylated Amides Based on the closo-Decaborate Anion

Abstract

Reactions between monocarbonylated [B₁₀H₉CO]^–closo-decaborate anion and N-nucleophiles have been studied. It has been discovered that not only primary and secondary, but also tertiary amines can enter the addition reactions. The C–N bond in the synthesized borylated amide derivatives has been found to be extremely labile and to cleave in an acidic medium to form the initial [B₁₀H₉CO]^– ion. In neutral aqueous solutions, borylated amides are hydrolyzed to form carboxylate derivatives with the general formula [B₁₀H₉COOH]^2–. All the synthesized derivatives have been separated out and studied by IR and NMR (¹H, ¹¹B, ¹³C) spectroscopy.