Journal of Structural Chemistry

, Volume 49, Issue 5, pp 965–968

X-Ray structural investigation of 1,3,6-trichloro-3,6-dimethylcycloheptanecarbonitrile and 2,5-dimethyl-2,5-dichlorohexane — Products of the reaction of 2,5-dimethyl-1,5-hexadiene with trichloroacetonitrile

  • A. A. Karapetyan
  • R. A. Tamazyan
  • A. R. Mikaelyan
  • A. M. Grigoryan
  • A. S. Vardanyan
  • L. Zh. Nikogosyan
Brief Communications

DOI: 10.1007/s10947-008-0166-5

Cite this article as:
Karapetyan, A.A., Tamazyan, R.A., Mikaelyan, A.R. et al. J Struct Chem (2008) 49: 965. doi:10.1007/s10947-008-0166-5

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.

Keywords

regio-and stereospecific intramolecular cyclization cycloheptanecarbonitrile 

Copyright information

© Pleiades Publishing, Ltd. 2008

Authors and Affiliations

  • A. A. Karapetyan
    • 1
  • R. A. Tamazyan
    • 1
  • A. R. Mikaelyan
    • 2
  • A. M. Grigoryan
    • 2
  • A. S. Vardanyan
    • 2
  • L. Zh. Nikogosyan
    • 2
  1. 1.Molecular Structure Research Center of Scientific — Technological Center of Organic and Pharmaceutical ChemistryNAS of ArmeniaErevanArmenia
  2. 2.State Engineering University of ArmeniaErevanArmenia