Synthesis 2006(13): 2100-2102  
DOI: 10.1055/s-2006-942408
PAPER
© Georg Thieme Verlag Stuttgart · New York

Chiral, Solvatochromic Schiff Bases Containing the (S)-Proline or (R)-3-Aminopropane-1,2-diol Functionality

Stefan Spange*, Katja Schreiter, Katja Hofmann
Department of Polymer Chemistry, Institute of Chemistry, Chemnitz University of Technology, 09111 Chemnitz, Germany
Fax: +49(371)5311642; e-Mail: stefan.spange@chemie.tu-chemnitz.de;
Further Information

Publication History

Received 26 April 2006
Publication Date:
08 June 2006 (online)

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.

17

Schreiter, K.; El Sayed, M.; Walfort, B.; Rüffer, T.; Lang, H.; Spange, S. unpublished results.

21

Spange, S.; Schreiter, K.; Hofmann, K. unpublished results.