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Original Articles

α-AMINOPHOSPHONATES BEARING FREE HYDROXYL GROUPS IN THE AROMATIC RINGS. SYNTHESIS AND NMR CHARACTERIZATION

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Pages 63-77 | Received 06 May 1997, Published online: 24 Sep 2006
 

Abstract

In this paper we describe a useful synthetic procedure leading in very good yields to mono- and bis-α-aminophosphonic acid dialkylesters containing the free phenolic hydroxyl group in a strategic position of the aromatic ring in order to enhance complexation with metal ions. This synthetic procedure is based on the addition of a solution of sodium dialkyl phosphite in phosphite to imine precursors. The addition reaction is highly stereospecific: only one diastereomer for each of the bis-α-aminophosphonic acid dialkylesters is formed. All compounds were characterized by NMR (1H and 31P) and by FAB-MS spectroscopy.

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