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Synthesis and Crystal Structure of 2-Amino-4,6,6-trimethyl-cyclohex-2-en-1,1,3,4(S)-tetracarbonitrile

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Abstract

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.

Graphical Abstract

Crystal structure analysis of the novel 2-amino-4,6,6-trimethyl-cyclohex-2-en-1,1,3,4(S)-tetracarbonitrile.

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References

  1. Zhang XM, Lu JT (2007) Acta Crystallogr E63:3861

    Google Scholar 

  2. Mehta G, Singh V (1999) Chem Rev 99:881

    Article  CAS  Google Scholar 

  3. Fillion E, Beingessner RL (2003) J Org Chem 68:9484

    Article  Google Scholar 

  4. Nakamura H, Aoyagi K, Shim JG, Yamamoto Y (2001) J Am Chem Soc 123:372

    Article  CAS  Google Scholar 

  5. Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079

    Article  CAS  Google Scholar 

  6. Wender PA, Rieck H, Fuji M (1998) J Am Chem Soc 120:10976

    Article  CAS  Google Scholar 

  7. Wender PA, Husfeld CO, Langkopf E, Love JA, Pleuss N (1998) Tetrahedron 54:7203

    Article  CAS  Google Scholar 

  8. Hollis TK, Odenkirk W, Robinson NP, Whelan J, Bosnich B (1993) Tetrahedron 49:5415

    Article  CAS  Google Scholar 

  9. Zeni G, Larock RC (2004) Chem Rev 104:2285

    Article  CAS  Google Scholar 

  10. Verma AK, Koul S, Pannu APS, Razdan TK (2007) Tetrahedron 63:8715

    Article  CAS  Google Scholar 

  11. Verma AK, Koul S, Razdan TK, Kapoor KK (2006) Can J Chem 84:1064

    Article  CAS  Google Scholar 

  12. Verma AK, Koul S, Razdan TK, Kapoor KK (2006) Tetrahedron Lett 47:837

    Article  Google Scholar 

  13. Verma AK, Koul S, Kapoor KK, Razdan TK (2007) Aust J Chem 60:883

    Article  CAS  Google Scholar 

  14. Sheldrick GM (1997) SHELX97. University of Gottingen, Gottingen

    Google Scholar 

  15. Farrugia LJ (1997) J Appl Crystallogr 30:565

    Article  CAS  Google Scholar 

  16. Farrugia J (1999) J Appl Crystallogr 32:837

    Article  CAS  Google Scholar 

  17. Nardelli M (1995) J Appl Crystallogr 28:659

    Article  CAS  Google Scholar 

  18. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans II:S1–S19

    Google Scholar 

  19. Duax WL, Norton DA (1975) Atlas of steroid structures, vol 1. Plenum, New York

    Google Scholar 

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Acknowledgment

The authors are thankful to Prof. P. K. Bharadwaj, Department of Chemistry, IIT, Kanpur, India, for the use of the data collection facility.

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Authors and Affiliations

  1. P.G. Department of Chemistry, University of Jammu, Jammu Tawi, 180 006, India

    Nitu Mahajan & T. K. Razdan

  2. P.G. Department of Physics, University of Jammu, Jammu Tawi, 180 006, India

    Pinki Kotwal & Vivek K. Gupta

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  1. Nitu Mahajan
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  2. Pinki Kotwal
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  3. Vivek K. Gupta
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  4. T. K. Razdan
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Correspondence to Vivek K. Gupta.

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Mahajan, N., Kotwal, P., Gupta, V.K. et al. Synthesis and Crystal Structure of 2-Amino-4,6,6-trimethyl-cyclohex-2-en-1,1,3,4(S)-tetracarbonitrile. J Chem Crystallogr 41, 742–746 (2011). https://doi.org/10.1007/s10870-010-9966-5

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  • DOI: https://doi.org/10.1007/s10870-010-9966-5

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