Synthesis and Crystal Structure of 2-Amino-4,6,6-trimethyl-cyclohex-2-en-1,1,3,4(S)-tetracarbonitrile
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Crystal structure analysis of the novel 2-amino-4,6,6-trimethyl-cyclohex-2-en-1,1,3,4(S)-tetracarbonitrile, obtained in 70% yield, by the Bi(OTf)3 catalyzed reaction of acetone and malononitrile, at room temperature, is described. For the first time Bi(OTf)3–Et3N has been used in this inverse electron demand Diels–Alder cycloaddition reaction involving the participation of carbonitrile π-bond. The structure of the molecule was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the monoclinic space group P21/n with unit cell parameters: a = 8.0580 (17), b = 13.038 (3), c = 12.641 (3) Å, β = 101.883 (4)°, Z = 4. The crystal structure was solved by direct methods and refined to R = 0.0506 for 2,456 observed reflections. The cyclohexene ring of the molecule adopts a distorted sofa conformation. The molecules in the unit cell are arranged in layers. The crystal structure in stabilized by C–H⋯N and N–H⋯N interactions.
KeywordsBismuth triflate-triethylamine Inverse electron demand Diels–Alder reaction Crystal structure Sofa Direct methods Hydrogen bonding
The authors are thankful to Prof. P. K. Bharadwaj, Department of Chemistry, IIT, Kanpur, India, for the use of the data collection facility.
- 1.Zhang XM, Lu JT (2007) Acta Crystallogr E63:3861Google Scholar
- 14.Sheldrick GM (1997) SHELX97. University of Gottingen, GottingenGoogle Scholar
- 18.Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans II:S1–S19Google Scholar
- 19.Duax WL, Norton DA (1975) Atlas of steroid structures, vol 1. Plenum, New YorkGoogle Scholar