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'2 5H Furanones' in keywords Facet   Publication Year 1999  [X]
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1999[X]
1Author    Saalfrank, JochenN. Achtrab, Stephan Reck, Frank HampelRequires cookie*
 Title    Synthese und Aggregatbildung eines 5-Hydroxy-2,5-dihydropyrrols. Enantiomerenreine, eindimensionale Stränge durch Wasserstoff- brückenbindungen und chiroselektive Selbstorganisation [1]  
 Abstract    Synthesis and A ggregation o f a 5-H ydroxy-2,5-dihydropyrrole. E nantiom erically Pure, O ne-dim ensional Strands via Hydrogen Bonds and Chiroselective S eif O rganization [ 1 ] R olf W. Reaction of dimethyl 1,3-acetonedicarboxylate 8 with oxalylchloride 2 and magnesium chlo­ ride as catalyst yielded 2,3-dioxo-2,3-dihydrofuran 9, which is in equilibrium with tautomer 10 (9:10 = 1:2). Addition of thionyl chloride to a mixture of 9/10 afforded 3-chloro-2(5H)-furanone 11. The structure of 11 was unequivocally established by X-ray diffraction, which indirectly pro­ ved the structure of 10 as well. Ring opening of 11 by nucleophilic attack with benzylamine 14 in C2-position and subsequent recyclization led to racemic 3-chloro-5-hydroxy-2-oxo-2,5-di-hydropyrrole 15. According to a single crystal X-ray analysis, 15 aggregates via stereospecific self selection through hydrogen bonds to give chiroselectively the one-dimensional strands 1 1(S)-15] and I [(R)-1SI 
  Reference    Z. Naturforsch. 54b, 179—186 (1999); eingegangen am 28. September 1998 
  Published    1999 
  Keywords    2(5H)-Furanones, Hydrogen-Bonding, Chiral Recognition, One-Dimensional Strand, Crystal Structure 
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 TEI-XML for    default:Reihe_B/54/ZNB-1999-54b-0179.pdf 
 Identifier    ZNB-1999-54b-0179 
 Volume    54