Optical Resolution of DL-2,2'-Bipiperidine through its Cobalt(III) Complex

Article abstract of DOI:10.1039/DT9850000895

The separation of racemic 2,2'-bipiperidine and the meso form has been performed through the dihydrochloride salt of the diamine.The reaction of racemic 2,2'-bipiperidine with 2)₆>^3- has been shown to yield only one DL pair of trans-bis(2,2'-bipiperidine)dinitrocobalt(III) complex ion.The dinitro-complex has been characterized and optically resolved using ammonium D-2-bromo-4,7-dimethyl-3-oxobicyclo<2.2.1>heptane-7-methanesulphonate.Optically pure (-)₅₈₉-2,2'-bipiperidine was recovered from the less soluble diastereoisomer and shows a specific rotation of -12.2 deg.The stereoselective formation of the trans-dinitro-complex is discussed in relation to the predictions of strain energy minimization calculations.

Full text of DOI:10.1039/DT9850000895

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