A. Karapetyan, R. Tamazyan, A. Mikaelyan
Nov 19, 2008
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Influential Citations
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Journal
Journal of Structural Chemistry
Abstract
Addition of trichloroacetonitrile to 2,5-dimethyl-1,5-hexadiene in the presence of cuprous amine complexes is studied. Single crystal X-ray diffraction unambiguously proves that the main product is a racemic mixture of the cyclic symmetric nitrile: (1r,3R,6S)-and (1r,3S,6R)-1,3,6-trichloro-3,6-dimethylcycloheptanecarbonitrile. Established relative configuration of the product confirms the ring closure mechanism suggested before. Also, a side product 2,5-dimethyl-2,5-dichlorohexane is isolated (the product of hydrochlorination of the starting alkadiene). Low-temperature (190 K) structural examination of this centrosymmetrical molecule indicates that the unit cell comprises one molecule.