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Silica-supported Phosphorus Chloride: An Efficient and Recyclable Catalyst for Beckmann Rearrangement of Ketoximes and Dehydration of Aldoximes Under Microwave Irradiation

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Abstract

Silica-supported phosphorus chloride has been proved to be an efficient and recyclable catalyst for Beckmann rearrangement of a variety of ketoximes and dehydration of various aldoximes in anhydrous THF under microwave irradiation. This protocol has advantages of high conversion, high selectivity, short reaction time, no environmental pollution, and simple work-up procedure.

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References

  1. Smith BM, March J (2001) Advanced organic chemistry, 5th ed. John Wiley & Sons: New York, p 1415 and references therein

  2. Nguyen MT, Raspoet G, Vanquickenborne LG (1997) J Chem Soc Perkin Trans 2:821

    Google Scholar 

  3. Kusama H, Yamashita Y, Narasaka K (1995) Bull Chem Soc Jpn 68:373

    Article  CAS  Google Scholar 

  4. Hill RK, Mckinnie BG, Conley RT, Darby PS, Vanhalbeek H, Holt EM (1988) Tetrahedron 44:3405

    Article  CAS  Google Scholar 

  5. Iglesias-Arteaga MA, Alvarado-Nuno AA (2006) Tetrahedron Lett 47:5351

    Article  CAS  Google Scholar 

  6. Yoo KH, Choi EB, Lee HK, Yeon GH, Yang HC, Pak CS (2006) Synthesis 1599

  7. Yan P, Batamack P, Prakash GKS, Olah G (2005) Catal Lett 103:165

    Article  CAS  Google Scholar 

  8. Tsuji H, Setoyama T (2005) Chem Lett 34:1232

    Article  CAS  Google Scholar 

  9. Zhu MZ, Cha CT, Deng WP, Shi XX (2006) Tetrahedron Lett 47:4861

    Article  CAS  Google Scholar 

  10. Boruah M, Konwar D (2002) J Org Chem 67:7138

    Article  CAS  Google Scholar 

  11. Furuya Y, Ishihara K, Yamamoto H (2005) J Am Chem Soc 127:11240

    Article  CAS  Google Scholar 

  12. Wang B, Gu YL, Luo C, Yang T, Yang LM, Suo JS (2004) Tetrahedron Lett 45:3369

    Article  CAS  Google Scholar 

  13. Chandrasekhar S, Gopalaiah K (2003) Tetrahedron Lett 44:7437

    Article  CAS  Google Scholar 

  14. Li DM, Shi F, Guo S, Deng YQ (2005) Tetrahedron Lett 46:671

    Article  CAS  Google Scholar 

  15. Yan P, Batamack P, Prakash GKS, Olah GA (2005) Catal Lett 101:141

    Article  CAS  Google Scholar 

  16. Thomas B, Prathapan S, Sugunan S (2005) Microporous Mesoporous Mater 79:21

    Article  CAS  Google Scholar 

  17. Sarvari MH (2005) Synthesis 787

  18. Movassagh B, Shokri S (2005) Synth Commun 35:887

    Article  CAS  Google Scholar 

  19. Yang SH, Chang S (2001) Org Lett 3:4209

    Article  CAS  Google Scholar 

  20. Attanasi O, Palma P, Serra-Zanetti F (1983) Synthesis 741

  21. (a) Li Z, Ding RB, Lu Z, Xiao SX, Ma XL (2006) J Mol Catal A: Chem 250:100 (b) Wang XG, Chen CC, Chen SY, Mou Y, Cheng SF (2005) Appl Catal A: Gen 281:47

  22. Dongare MK, Bhagwat VV, Ramana CV, Gurjar MK (2004) Tetrahedron Lett 45:4759

    Article  CAS  Google Scholar 

  23. (a) Curtis MP, Bunnelle WH, Pagano TG, Gopalakrishnan M, Faghih R (2006) Synth Commun 36:321; (b) Moghaddam FM, Rad AAR, Zali-Boinee H (2004) Synth Commun 34:2071; (c) Thakur AJ, Boruah A, Prajapati D, Sandhu JS (2000) Synth Commun 30:2105; (d) Feng JC, Liu B, Dai L, Bian NS (1998) Chin Chem Lett 9:795; (e) Loupy A, Regnier S (1999) Tetrahedron Lett 40:6221; (f) Hegedues A, Cwik A, Hell Z, Horvath Z, Esek A, Uzsoki M (2002) Green Chem 4:618; (g) Lingaiah N, Narender R (2002) Synth Commun 32:2391; (h) Dewan S, Singh R (2003) Synth Commun 33:3085; (i) Kumar HS, Mohanty PK, Kumar MS, Yadav JS (1997) Synth Commun 27:1327

  24. Xu T, Kob N, Drago RS (1997) J Am Chem Soc 119:12231

    Article  CAS  Google Scholar 

  25. Morrow BA, Lang SJ (1994) Langmuir 10:756

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the Gansu Natural Foundation (3ZS061-A25–033), ‘Chunhui Project’ of the Ministry of Education of China (Z2004-1-62034), and Key Laboratory of Eco-Environment-Related Polymer Materials (Northwest Normal University) for the financial support of this work.

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Authors and Affiliations

  1. Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P.R. China

    Zheng Li, Zhong Lu, Anguo Zhu, Xu Feng, Jing Liu & Guoqiang Tian

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  1. Zheng Li
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  2. Zhong Lu
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  3. Anguo Zhu
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  4. Xu Feng
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  5. Jing Liu
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Correspondence to Zheng Li.

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Li, Z., Lu, Z., Zhu, A. et al. Silica-supported Phosphorus Chloride: An Efficient and Recyclable Catalyst for Beckmann Rearrangement of Ketoximes and Dehydration of Aldoximes Under Microwave Irradiation. Catal Lett 120, 100–105 (2008). https://doi.org/10.1007/s10562-007-9258-7

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  • DOI: https://doi.org/10.1007/s10562-007-9258-7

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