Mechanism of oxidation of alcohols by aqueous bromine

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

“…[54] Benzyl methyl ethers were almost exclusively prepared by the classical Williamson synthesis, by treatment of an MeOH solution of the appropriate halide (100.0 mmol in 100 mL) with MeONa in MeOH (200 mmol in 100 mL), by a described procedure (Method A). [55] 1-(Methoxymethyl)-3-methylbenzene (1c, 11.02 g, 81% from the chloride), [56] 1-(1,1-dimethylethyl)-4-(methoxymethyl)benzene (1e, 14.60 g, 82% from the bromide), [57] 1-chloro-2-(methoxymethyl)benzene (1f, 11.70 g, 75% from the chloride), [58] 1-chloro-3-(methoxymethyl)benzene (1g, 12.48 g, 80% from the chloride), [58] 1-chloro-4-(methoxymethyl)benzene (1h, 12.17 g, 78% from the chloride), [59] 1,3-dichloro-4-(methoxymethyl)benzene (1j, 17.57 g, 92% from the chloride), [60] 1-(methoxymethyl)-2-nitrobenzene (1k, 12.53 g, 75% from the iodide), [61] 1-(methoxymethyl)-3-nitrobenzene (1m, 13.03 g, 78% from the iodide), [62] 1-(methoxymethyl)-4-nitrobenzene (1n, 12.69 g, 76% from the iodide), [62] and diphenylmethyl methyl ether (1hh, 17.62 g, 89% from the chloride) [63] were prepared by Method A. [(1,1-Dimethylethoxy)methyl]benzene [64] (1dd, 7.22 g, 44%) was prepared in a similar way, from benzyl bromide and potassium tert-butoxide.…”

Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?

“…A literature survey suggested that such secondary versus primary selectivity was common in RBS-mediated alcohol oxidation . For example, N -bromo acetamide, N -bromo succinimide, and elemental bromine were reported to selectively oxidize the secondary alcohol in the presence of a primary alcohol − (Scheme ), which was believed to proceed through the RBS-based oxidation mechanism. − Considering these precedents, we believed that the FeBr 3 /H 2 O 2 system should involve a similar RBS-based mechanism to achieve the selective oxidation of secondary alcohols.…”

Electrochemical Hydrodimerization of Furfural in Organic Media as an Efficient Route to Jet Fuel Precursor

“…Thus, more than a half of furfural was converted to another products. Since the consumption of hydrofuroin was observed during the electrolysis, it is plausible that it can undergo oxidation by Br 2 formed at the anode, which is a known process for diols [41,42] . In addition, the formation of a polymeric film on the electrode surface was observed in the experiments (Figure S7), indicating that furfural or its reduction products were consumed to form this film.…”