Supplementary Material

Selective oxidation of organic substrates in presence of H2O2 using a polymer-anchored iron(III)-ferrocene complex

Sk Manirul Islam*, Sumantra Paul, Anupam Singha Roy, paramita Mondal

Department of Chemistry, University of Kalyani, Kalyani, Nadia, 741235, W.B., India.

Corresponding author’s E-mail:

A. Spectral data of products

NMR data of oxidation products of alkane

  1. 1-adamantanol[1]: 1H NMR (CDCl3) δ (ppm) 4.10 (s, 1H), 2.10-2.14 (m, 3H) 1.94-1.98 (m, 6H), 1.77-1.80 (m, 6H); 13C NMR (CDCl3) δ (ppm) 67.9, 45.8, 37.1, 31.9.
  2. Benzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 10.17 (s, 1H), 7.91 (d, 2H), 7.63 (m, 1H), 7.51 (m, 2H); 13C NMR (CDCl3) δ (ppm) 192.6, 136.1, 133.9, 130.1, 129.3.
  3. 4-Nitrobenzaldehyde[3]: 1H NMR (CDCl3) δ (ppm) 10.14 (s, 1H), 8.39 (d, 2H), 8.06 (d, 2H); 13C NMR (CDCl3) δ (ppm) 192.3, 154.2, 143.5, 130.6, 124.8.
  4. 4-Chlorobenzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 10.13 (s, 1H), 7.85 (d, 2H), 7.58 (d, 2H); 13C NMR (CDCl3) δ (ppm) 191.0, 141.1, 134.9, 131.1, 129.6.
  5. Acetophenone[4]: 1H NMR (CDCl3) δ (ppm) 7.92 (m, 2H), 7.52 (m, 1H), 7.46 (m, 2H), 2.55 (s, 3H); 13C NMR (CDCl3) δ (ppm) 198.1, 137.4, 133.2, 128.5, 128.2, 26.6.
  6. Propiophenone[5]: 1H NMR (CDCl3) δ (ppm) 7.95 (d, 2H), 7.59 (m, 1H), 7.52 (m, 2H), 3.10 (m, 2H), 1.20 (t, 3H); 13C NMR (CDCl3) δ (ppm) 200.8, 136.9, 133.0, 128.9, 128.4 128.1, 127.8, 31.7, 8.09.
  7. 4-Chloroacetophenone[4]: 1H NMR (CDCl3) δ (ppm) 7.86 (d, 2H), 7.41 (d, 2H), 2.59 (s, 3H); 13C NMR (CDCl3) δ (ppm) 196.6, 139.5, 135.5, 129.8, 128.6, 26.4.
  8. 4-Methoxyacetophenone[4]: 1H NMR (CDCl3) δ (ppm) 7.95 (d, 2H), 6.94 (d, 2H), 3.85 (s, 3H), 2.55 (s, 3H); 13C NMR (CDCl3) δ (ppm) 196.6, 160.1, 130.4, 129.8, 113.8, 55.6, 26.1.
  9. 4-Methylacetophenone[4]: 1H NMR (CDCl3) δ (ppm) 7.85 (d, 2H),7.24 (d, 2H), 2.57 (s, 3H), 2.40 (s, 3H); 13C NMR (CDCl3) δ (ppm) 197.6, 144.0, 134.6, 129.1, 128.3, 26.4, 21.5.
  10. Benzophenone[5]: 1H NMR (CDCl3) δ (ppm) 7.84 (d, 4H), 7.68 (m, 2H), 7.57 (m, 4H); 13C NMR (CDCl3) δ (ppm) 197.0, 137.8, 132.5, 130.0, 127.9.
  11. 2-Octanone[4]: 1H NMR (CDCl3) δ (ppm) 2.36 (t, 2H), 2.12 (s, 3H), 1.53 (m, 2H), 1.22 (m, 6H), 0.85(q, 3H); 13C NMR (CDCl3) δ (ppm) 209.2, 43.6, 31.5, 30.0, 28.7, 23.7, 22.6, 14.2.
  12. Cyclohexanone[5]: 1H NMR (CDCl3) δ (ppm) 2.29 (t, 4H), 1.86 (m, 4H), 1.71 (m, 2H); 13C NMR (CDCl3) δ (ppm) 211.1, 41.9, 27.0, 24.9
  13. 2-Phenylcyclohexanone [6]: 1H NMR (CDCl3) δ (ppm) 7.31-7.40 (m, 2 H), 7.18-7.22 (m, 1 H), 7.08-7.10 (m, 2 H), 3.60 (dd, 1 H), 2.48-2.57 (m, 2 H), 2.24-2.30 (m, 1 H),2.09-2.14 (m, 1 H), 1.89-2.00 (m, 2 H), 1.75-1.80 (m, 2 H); 13C NMR (CDCl3) δ (ppm) 211.0, 138.9, 129.1, 128.4, 126.9, 58.0, 42.1, 35.2, 27.9, 26.0
  14. 2-Phenylcyclopentanone [7]:1H NMR (CDCl3) δ (ppm) 7.19-7.38 (m, 5H), 3.09-3.49 (m, 1H), 1.73-2.57 (m, 6H); 13C NMR (CDCl3) δ (ppm) 216.8, 138.2, 128.1, 127.7, 126.0, 54.4, 37.7, 32.0, 19.9
  15. 1-Indanone [8]:1H NMR (CDCl3) δ (ppm)2.59 (t, 2H), 3.12 (t, 2H), 7.11–7.76 (m, 4H); 13C NMR (CDCl3) δ (ppm) 205.7, 154.9, 137.1, 129.8, 127.2, 126.9, 126.0, 35.7, 26.1
  16. α-Tetralone [8]: 1H NMR (CDCl3) δ (ppm) 1.99–2.20 (m, 2H), 2.47–2.59 (m, 2H), 2.79–3.00 (m, 2H), 7.18–8.06 (m, 4H); 13C NMR (CDCl3) δ (ppm) 200.1, 141.8, 134.1, 132.9, 127.6, 126.9, 125.6, 40.1, 30.3, 23.0

NMR data of oxidation products of alcohols

  1. Benzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 10.16 (s, 1H), 7.90 (d, 2H), 7.62 (m, 1H) 7.52 (m, 2H); 13C NMR (CDCl3) δ (ppm) 192.5, 136.2, 133.8, 130.2, 129.1.
  2. 2-Methoxybenzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 9.98 (s, 1H), 7.61 (d, 1H), 7.51 (m, 1H), 7.30 (m, 1H), 7.16 (d, 1H), 3.79 (s, 3H); 13C NMR (CDCl3) δ (ppm) 192.1, 164.1, 136.1, 131.2, 124.9, 121.6, 111.9, 55.7.
  3. 4-Chlorobenzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 10.11 (s, 1H), 7.84 (d, 2H), 7.60 (d, 2H); 13C NMR (CDCl3) δ (ppm) 191.1, 141.0, 134.8, 131.2, 129.4.
  4. 4-Nitrobenzaldehyde[3]: 1H NMR (CDCl3) δ (ppm) 10.13 (s, 1H), 8.40 (d, 2H), 8.08 (d, 2H); 13C NMR (CDCl3) δ (ppm) 192.5, 154.1, 143.4, 130.5, 124.7.
  5. 4-Bromobenzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 9.8 (s, 1H), 7.72-7.85 (m, 4H); 13C NMR (CDCl3) δ (ppm) 191.9, 135.3, 132.3, 130.7, 129.5.
  6. 2-Chlorobenzaldehyde[2]: 1H NMR (CDCl3) δ (ppm) 10.44 (s, 1H), 7.89 (d, 1H), 7.44-7.60 (m, 3H); 13C NMR (CDCl3) δ (ppm) 189.2, 137.5, 135.2, 134.1, 131.1, 130.8, 127.7.
  7. Cyclohexanone[2]: 1H NMR (CDCl3) δ (ppm) 2.28 (t, 4H), 1.85 (m, 4H), 1.70 (m, 2H); 13C NMR (CDCl3) δ (ppm) 211.0, 41.8, 27.1, 24.7.
  8. Benzophenone[2]: 1H NMR (CDCl3) δ (ppm) 7.84 (d, 4H), 7.68 (m, 2H), 7.57 (m, 4H); 13C NMR (CDCl3) δ (ppm) 197.0, 137.8, 132.5, 130.0, 127.9.
  9. Benzil[9]: 1H NMR (CDCl3) δ (ppm) 7.99 (d, 4H,), 7.65-7.69 (m, 2H), 7.51-7.56 (m, 4H); 13C NMR (CDCl3) δ (ppm) 194.56, 134.87, 133.0, 129.94, 129.01.
  10. Acetone[10]: 1H NMR (CDCl3) δ (ppm) 2.15 (s, 6H); 13C NMR (CDCl3) δ (ppm) 207.02, 30.97.
  11. Acetophenone[4]: 1H NMR (CDCl3) δ (ppm) 7.91 (m, 2H), 7.52 (m, 1H), 7.45 (m, 2H), 2.54 (s, 3H); 13C NMR (CDCl3) δ (ppm) 198.0, 137.3, 133.1, 128.4, 128.1, 26.6.
  12. 2,2-Dimethylpropiophenone[5]: 1H NMR (CDCl3) δ (ppm) 7.61 (d, 2H), 7.20-7.52 (m, 3H), 1.25 (s, 9H); 13C NMR (CDCl3) δ (ppm) 210.1, 138.3, 130.9, 127.5, 127.3, 44.4, 28.1.

References

[1] K. Wang, R. Cui, J. Gu, O. Yu, G. Ma, J. Nie, J. Appl. Polym. Sci.123, 26 (2012).

[2] V. Polshettiwar, R. S. Varma, Org. Biomol. Chem.7, 37 (2009).

[3] Y. Xie, W. Mo, D. Xu, Z. Shen, N. Sun, B. Hu, X. Hu, J. Org. Chem.72, 4288 (2007).

[4] J-L. Wang, L-N. He, C-X. Miao,Y-N.Li,Green Chem.11, 1317 (2009).

[5]D.F. Brayton, C. Mocka, C. Berini, O. Navarro, Org. Lett.11, 5094 (2009).

[6] R. P. Santos, R. S. Lopes,C. C. Lopes, Synthesis.845 (2001).

[7] J. Tercio, B. Ferreira, W. O. Cruz, P. C. Vieira, M. Yonashiro, J. Org. Chem. 52(16),

(1987) 3698.

[8] A. Shaabani, A. Bazgir, F. Teimouri, D. G. Lee, Tetrahedron Letters 43,5165 (2002)

[9] M. Hanif, L.U. Ping, G.U. Cheng, W.Z. Ming, Y.S. Min, Y. Bing, W.C. Lei, M.Y. Guang,

Chem. Res. Chinese Universities25, 950 (2009).

[10] H.E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem.62, 7512 (1997).