S. Spange, K. Schreiter, Katja Hofmann
Jul 1, 2006
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Synthesis
Abstract
Chiral 4-nitroaniline derivatives 2a,b containing amino acid and 1,2-diol functionalities have been synthesized by specific nucleophilic substitution of 1-fluoro-4-nitrobenzene (1) with (S)-proline or (R)-3-aminopropane- 1,2-diol. Following reduction of the nitro groups under very mild conditions, the corresponding p-phenylenediamine derivatives 3a,b were obtained which are very sensitive to oxidation. Thus, 3a,b were converted in situ into chiral, solvatochromic Schiff bases.