Ultrasound Assisted Nitratobis (Triphenyl phosphine) Copper (I) catalyzed Addition of Organocadmium Reagents to α, β-Unsaturated Cyanoester

Authors

  • Ashok S. Pise  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Arvind S. Burungale  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Ramesh B. Gawade  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Santosh S. Devkate  Department of Chemistry, Mahatma Phule Mahavidyalaya, Panvel, Raigad, Maharashtra, India
  • Sunil D. Jadhav  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Shripad M. Patil  

Keywords:

Conjugate addition, Cyanoester, Cu (I) catalyst, Grignard reagent, Ultrasound irradiation.

Abstract

Treatment of α, β-unsaturated cyanoester with phenyl cadmium bromide, derived from dilithium tetrachloro cadmium (Li2CdCl4) and Grignard reagent in the presence of 10 mol % of Nitratobis (Triphenyl phosphine) Copper (I) i.e. Cu(PPh3)2NO3 catalyst afforded chemoselective conjugated product in high yields.

References

  1. W. Richards, Loomis A. J. Am. Chem. Soc. (1927), 49, 3086.
  2. J. L. Luche J. Chem. Society, Chem. Comm. (1992), 798-799.
  3. J. L. Luche Synthetic Communication, (1991), 21, 643-651.
  4. A. Commercon, M. Bourgain, M. Delaumeny, J. F. Normant & J. Villieras, (1975), 16, 3837.
  5. P. Barsantai, V. Calo, L. Lopez, G. Marchese, F. Naso &G. Pesce, J. Chem Soc. Chem Commun, (1978), 1085.
  6. C. C. Tseng, S. D. Paisley and H. L. Goering, J. Org. Chem, (1986), 51, 2884.
  7. J. E. Backvall, M. Sellen and B. Grant, J. Am. Chem. Soc. (1990), 112, 6615.
  8. J. E. Backvall, E. S. M. Persson and A. Bombrun, J. Org. Chem, (1994), 59, 4126.
  9. E. S. M. Persson, M. Van Klaveren, D. M. Grove and J, E. Backvall, Chem Eur J. (1995), 1. 351.
  10. M. B. Deshmukh, S. D. Jadhav, A. R. Mali, A. W. Suryawanshi, P. V. Anbhule, S. S. Jagtap and S. A. Deshmukh, Synth. Commn, (2005), 35. 2967.
  11. M. B. Deshmukh, S. D. Jadhav, A. R. Mali, A. W. Suryawanshi, P. V. Anbhule, J. Chem Res.
  12. M. B. Deshmukh, S. D. Jadhav, and S. V. Kadam, Indian Journal of Chemistry, (2007), 46B, 989-994.
  13. W. J. Houlihan, Indoles, (John Wiley and Sons Inc, New York ) 1972.
  14. Ji-Tai Li, Zhi-Ping Lin andCai Tong Liu, Indian Journal of Chemistry, (2008), 47B, 283-290.
  15. D. Kanwar, R. Rani J. Agarwal and R. K. Peddinti, Indian Journal of Chemistry, (2010), 49B, 1290-1299.
  16. V. Kumar, S. Kaur and S. Kumar, Tetrahedron Lett, (2007), 47, 7001.
  17. P. Armugam and P. T. Perumal, Chem Lett, (2006), 35, 632.
  18. A. Arcadi, G. Bianchi, M. Chiarini, F. Marinelli, Synlett, (2004), 944.
  19. G. Bartoli, M. Bartolacci, M. Bosco, G. Foglia, A. Giuliani, E. Marcantoni L. Sambri and E. Torregiani, J. Org. Chem. (2003), 68, 4594.
  20. W. J. Li, X-F Lin, J. Wang G-L Li and Y-G Wang, Synlett, (2006),2003.
  21. M. Bandini, P. G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva and A. Umani-Ronchi, J. Org. Chem, (2002), 67, 3700.
  22. Z, H. Huang, J. P. Zou andW. Q. Jiang, Tetrahedron Lett, (2006), 47, 7965.
  23. Z-P. Zhan, R-F Yang and K. Lang, Tetrahedron Lett, (2005), 46, 3839.
  24. Z. Li, Z. Shi & C. He, J. Organomet. Chem, (2005), 5049)
  25. J. S. Yadav B, V. S. Reddy G. Baishya, K.V. Reddy abd A. V. Narsaiah, Tetrahedron Lett, (2005), 61, 9541. 
  26. C. A. M. A. Hug andA. R. Naresh Raj, , Indian Journal of Chemistry, (2013), 52B, 1451-1454.
  27. S. Kotha and R. Ali, Indian Journal of Chemistry, (2016), 55B, 1099-1106.
  28. E. Korkusuz and I. Yildirim, Indian Journal of Chemistry, (2017), 56B, 152-159.

International Journal of Scientific Research in Science and Technology

Downloads

Published

2018-02-28

Issue

Volume 4, Issue 2, January-February-2018

Section

Research Articles

License

Copyright (c) IJSRST

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
Ashok S. Pise, Arvind S. Burungale, Ramesh B. Gawade, Santosh S. Devkate, Sunil D. Jadhav, Shripad M. Patil "Ultrasound Assisted Nitratobis (Triphenyl phosphine) Copper (I) catalyzed Addition of Organocadmium Reagents to α, β-Unsaturated Cyanoester" International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011,Volume 4, Issue 2, pp.121-124, January-February-2018.