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- In a typical experiment, the oxime (3 mmols) was dissolved in acetone 5 mL and sodium tungstate (10-mol%) was added to it. The reaction mixture was cooled to −5°C in ice-salt mixture. To a stirred mixture of the above 1.5 mL of H2O2 was added dropwise. The reaction was monitored by TLC and the solvent was removed and water added to the residue. The mixture was extracted with ether, combined ether extracts were washed with 5% Na2S2O3, water and dried over anhydrous sodium sulfate. Evaporation of the solvent gives crude carbonyl compound, which is further purified by crystallization/distillation. Analytical data for new compounds is given below: 5. Oxime: M.p. 234–236°C. 1H NMR (200 MHz, CDCl3): δ 7.15 (d, J = 6 Hz, 2H, ArH); 7.65 (d, J = 6 Hz, 2H, ArH), 7.85 (s, 1H, ArH); 8.10 (s, 1H, CH=NH). EIMS m/z: 318 (M+). Aldehyde: M.p. 123–124°C. 1H NMR (200 MHz, CDCl3): δ 7.3 (d, J = 6 Hz, 2H, ArH), 7.8 (s, 1H, ArH), 7.9 (d, J = 6 Hz, 2H, ArH), 10.0 (s, 1H, CHO). IR (KBr) ν = 1413, 1698 cm−1. EIMS: 303 (M+). 13. Oxime 1H NMR (200 MHz, CDCl3): δ 2.0 (s, 3H, CH3), 6.75 (s, 1H, CH=CH), 7.1 (d, J = 6 Hz, 2H, ArH), 7.5 (m, 3H, ArH & CH=CH), 7.8 (s, 1H, ArH). IR (KBr) ν = 3286, 3124, 2897, 1536, 1406, 1167 cm−1. Ketone.1H NMR (200 MHz, CDCl3): δ 2.4 (s, 3H, CH3), 6.70 (d, J = 10 Hz, 1H, CH=CH), 7.2 (d, J = 6 Hz, 2H, ArH), 7.5 (d, 1H, J = 10 Hz, CH=CH), 7.6 (d, J = 6 Hz, 2H, ArH), 7.85 (s, 1H, ArH). IR (KBr) ν = 3102, 1654, 1502, 1403, 1178 cm−1. EIMS: 343 (M+)