Beckmann Rearrangement of Oximes Using Doped Silica Gel Complex

Y. Umanadh; N. Srinivasa Reddy; Khagga Mukkanti; G. Omprakash

doi:10.14233/ajchem.2015.17170

Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Issue Published : February 4, 2015

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

Beckmann Rearrangement of Oximes Using Doped Silica Gel Complex

https://doi.org/10.14233/ajchem.2015.17170

Y. Umanadh

Pharma Zell R&D (India) Private Limited, Visakhapatnam-531 162, India; Institute of Science & Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad- 500 072, India

N. Srinivasa Reddy

Pharma Zell R&D (India) Private Limited, Visakhapatnam-531 162, India

Khagga Mukkanti

Institute of Science & Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad- 500 072, India

G. Omprakash

Pharma Zell R&D (India) Private Limited, Visakhapatnam-531 162, India

Corresponding Author(s) : Y. Umanadh

yepuri.umanath@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 4 (2015): Vol 27 Issue 4
Article Published : February 3, 2015

Abstract

A new complex of perchloric acid absorbed on silica gel (doped silica gel) and dichloromethane was found to be very effective for converting ketoximes into their corresponding amides or lactams with excellent conversion via the Beckmann rearrangement. This method offers significant advantages such as efficiency and mild reaction conditions with shorter reaction time.

Keywords

Doped silica gel/dichloromethane Beckmann rearrangement Ketoximes Amides

Umanadh, Y., Srinivasa Reddy, N., Mukkanti, K., & Omprakash, G. (2015). Beckmann Rearrangement of Oximes Using Doped Silica Gel Complex. Asian Journal of Chemistry, 27(4), 1209–1211. https://doi.org/10.14233/ajchem.2015.17170

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References

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References

(a) H. Olivier-Bourbigou and L. Magna, J. Mol. Catal., 182–183, 419 (2002); doi:10.1016/S1381-1169(01)00465-4; (b) J.S. Yadav, B.V.S. Reddy, C.S. Reddy and K. Rajasekhar, J. Org. Chem., 68, 2525 (2003); doi:10.1021/jo026544w; (c) C.E. Song and E. Roh, J. Chem. Commun., 837 (2000); doi:10.1039/b001403f; (d) Y. Chauvin, L. Mussmann and H. Olivier, Angew. Chem. Int. Ed. Engl., 34, 2698 (1996); doi:10.1002/anie.199526981.

(a) M.J. Climent, A. Corma and S. Iborra, J. Mol. Catal., 233, 308 (2005); doi:10.1016/j.jcat.2005.05.003; (b) Y.M. Chung and H.K. Rhee, J. Mol. Catal., 159, 389 (2000); doi:10.1016/S1381-1169(00)00226-0.

(a) N.A. Owston, A.J. Parker and J.M. Williams, J. Org. Lett., 9, 73 (2007); doi:10.1021/ol062549u; (b) N.A. Owston, A.J. Parker and J.M. Williams, J. Org. Lett., 9, 3599 (2007); doi:10.1021/ol701445n; (c) S. Park, Y.- Choi, H. Han, S. Ha Yang and S. Chang, Chem. Commun., 1936 (2003); doi:10.1039/b305268k.

Y. Izumi, S. Sato and K. Urabe, Chem. Lett., 12, 1649 (1983); doi:10.1246/cl.1983.1649.

S. Chandrasekhar and K. Gopalaiah, Tetrahedron Lett., 44, 755 (2003); doi:10.1016/S0040-4039(02)02644-8.

S. Chandrasekhar and K. Gopalaiah, Tetrahedron Lett., 43, 2455 (2002); doi:10.1016/S0040-4039(02)00282-4.

B. Wang, Y. Gu, C. Luo, T. Yang, L. Yang and J. Suo, Tetrahedron Lett., 45, 3369 (2004); doi:10.1016/j.tetlet.2004.03.017.

D. Li, F. Shi, S. Guo and Y. Deng, Tetrahedron Lett., 46, 671 (2005); doi:10.1016/j.tetlet.2004.11.116.

L. De Luca, G. Giacomelli and A. Porcheddu, J. Org. Chem., 67, 6272 (2002); doi:10.1021/jo025960d.

R. Anilkumar and S. Chandrasekhar, Tetrahedron Lett., 41, 5427 (2000); doi:10.1016/S0040-4039(00)00875-3.

(a) M.M. Heravi, K. Bakhtiari and H.A. Oskooie, J. Chem. Res., 2005, 590 (2005); doi:10.3184/030823405774309005; b A.V. Narsaiah and K. Nagaiah, Adv. Synth. Catal., 346, 1271 (2004); doi:10.1002/adsc.200404059.

(a) A.R. Katritzky, G.F. Zhang and W.G. Fan, Org. Prep. Proced. Int., 25, 315 (1993); doi:10.1080/00304949309457966; (b) G. Sosnovsky and J.A. Krogh, Synthesis, 1978, 703 (1978); doi:10.1055/s-1978-24868; (c) A. Saednya, Synthesis, 748 (1983); doi:10.1055/s-1983-30499; (d) P. Molina, M. Alajarin and M.J. Vilaplana, Synthesis, 1016 (1982); doi:10.1055/s-1982-30044.

(a) W.C. Li, A.H. Lu, R. Palkovits, W. Schmidt, B. Spliethoff and F. Schuth, J. Am. Chem. Soc., 127, 12595 (2005); doi:10.1021/ja052693v; (b) H. Ichihashi and M. Kitamura, Catal. Today, 73, 23 (2002); doi:10.1016/S0920-5861(01)00514-4; (c) K.V.N.S. Srinivas, E.B. Reddy and B. Das, Synlett, 625 (2002); doi:10.1055/s-2002-22701.

A.K. Chakraborti and R. Gulhane, Chem. Commun., 1896 (2003); doi:10.1039/b304178f.

Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Beckmann Rearrangement of Oximes Using Doped Silica Gel Complex

Corresponding Author(s) : Y. Umanadh

Abstract

Keywords

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