Syntheses and characterization of (N→B)phenyl[N-arylaminodiacetate-O,O′,N]boranes and N-arylaminodiacetic acids

✍ Scribed by Teresa Mancilla; Ma. de Lourdes Alarcón; Lourdes Carrillo

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 626 KB
• Volume: 5
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520050507

✦ Synopsis

Abstract

The (N→B)phenyl[iminodiacetate‐O,O′,N]borane 1 is stable to hydrolysis, and the fact that the N‐H proton has been shown to be more acidic than the α‐protons to the carbonyl groups has led to the syntheses of N‐substituted boron heterocycles. Thus, the reactions of compound 1 with 2,2,6,6‐tetramethylpiperidine and aryl halides led to the syntheses of (N→B)phenyl[N‐arylaminodiacetate‐O,O′,N]boranes 2–9, which were, in turn, hydrolyzed to afford the corresponding N‐arylaminodiacetic acids 10–17. All compounds studied in this work were characterized by ^1^H, ^13^C, and ^11^B (for boron compounds) NMR, infrared, and mass spectroscopy.