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Search for Conglomerate in Set of [7]Helquat Salts: Multigram Resolution of Helicene-Viologen Hybrid by Preferential Crystallization

  作者 VAVRA JAN; SEVERA LUKAS; CISAROVA IVANA; KLEPETAROVA BLANKA; SAMAN DAVID; KOVAL DUSAN; KASICKA VACLAV; TEPLY FILIP  
  选自 期刊  Journal of Organic Chemistry;  卷期  2013年78-4;  页码  1329-1342  
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[摘要]Investigation of a set of 12 [7]helquat salts by X-ray crystal diffraction led to identification of conglomerate behavior in bis(trifluoroacetate) salt [2][CF3CO2](2). This is to demonstrate that a systematic search for conglomerates can be performed for a given helicenoid enabling straightforward multigram resolution via preferential crystallization. Subsequently, preferential crystallization of this chiral helicene viologen hybrid has been established to obtain pure P and M enantiomers on a multigram scale, 5 g each. Furthermore, preparation of nonracemic samples of [7]helquat 2 via diastereomeric (R,R)-dibenzoyltartrate salts is described, and determination of absolute configuration and racemization barrier is also reported.

 
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