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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 20
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Original Articles

ONE-POT OXIDATION OF AZOMETHINE COMPOUNDS INTO ARENECARBOXYLIC ACIDS

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Pages 3151-3159 | Received 02 Jan 2001, Published online: 16 Aug 2006

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  • When other solvent such as acetic acid, methanol, dioxane and tert-butanol was used, the reaction was slower and oxidation was less selective
  • The diselenides tested as catalyst, such as 2- and 4-pyridyl, 6-methyl-2-pyridyl, 2-quinolyl, 5-pyrimidinyl, 2- and 4-nitrophenyl and poly(bis-9, 10-anthracenyl) diselenide (PADS) were synthesized according to the ref.[6], [13a], [13b], [13c], [13d] Synthesis of diselenide RSeSeR (R: 3-nitro-2-pyridyl, 2-nitrio-4(trifluoromethyl)phenyl, 2-(trifluoromethyl) phenyl (bis-1,4-phenylene) and benzene-1,2-diseleninic acid will be published in due course. Selenium dioxide and diphenyl diselenide were purchased from Aldrich. Poly (bis-1,2-phenylene) diselenide (6) was synthesized in the way reported
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  • The compound 9 was isolated in the 24% yield[16] from mixture 2t and 9 by using column chromatography. Colorless prisms, mp = 149.5–150.5°C (toluene), lit.[17] mp = 150–151°C. IR (KBr): 3500–2200 cm−1 (COOH), 1759 and 1709 cm−1 (C=O). 1H NMR (CDCl3): 8.30 (s, 1H, COOH), 7.93 (d, 1H, J = 7.5 Hz, ArH), 7.72 (t, 1H, J = 7.5 Hz, ArH), 7.58 (t, 1H, J = 7.5 Hz, ArH), 7.54 (d, 1H, J = 7.5 Hz, ArH), 5.80 (t, 1H, J = 6.5 Hz, CH), 2.99 (d, 2H, J = 6.5 Hz, CH2). 13C NMR data are identical as these reported in ref.[18]
  • The compd. 9 was also obtained in 26% yield by the oxidation of 1-naphtol
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  • Said S.B private communication to be published
  • Toxicity of poly(bis-1,2-phenylene) diselenide (6) is unknown. According to know rules its toxicity should be low.24-25 Nevertheless avoid skin contact by use of gloves. All manipulations should be done in a hood
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  • 1,2-Diiodobenzene was easily prepared (85% yield) in molar scale by conversion of 2-iodoaniline to diazonium salt by treatment with acidic sodium nitrite in acetic acid solution and subsequent reaction with aqueous sodium iodide. From the solution 1,2-diiodobenzene was extracted with dichloromethane and purified by destillation in vacuo at 152°/15 mm

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