Oxidation of Benzoin to Benzil Using Burgess Reagent

Zinc azaphthalocyanines with thiophen-2-yl, 5-methylthiophen-2-yl and pyridin-3-yl peripheral substituents: Additive substituent contributions to singlet oxygen production

“…No physical data were given for 3,3 0 -pyridoin [21], but presumably the compound was obtained from a benzoin condensation. Burgess reagent was reported to oxidize 2,2 0 -pyridoin [32,33] and might be used for oxidation of 3,3 0 -pyridoin as well. The formation of bis-anils from aromatic carboxaldehydes, and subsequent acid hydrolysis to a-diketones was reported for aromatic compounds in general [31] and specifically for 1b [19].…”

“…However, the remaining yellow oil did not crystallize, probably due to the presence of two minor, unidentified compounds, and the expected pyridoin racemate. Various methods [16,30,32] were tested for oxidation of the crude pyridoin, but the resulting product mixtures were not easily purified. The cleanest oxidation was obtained from a reaction of the pyridoin with activated alumina at 140 C [36].…”

Microwave assisted solvent free oxidation of hydrobenzoins, benzoins and alcohols with NBS – Al2O3

“…Hydrobenzoins and benzoins have also been oxidized with Bi(NO 3 )-Cu(OAc) 2 , 7 RuCl 3 /Bromamine-T, 8 the Burgess reagent, 9 NBS/CCl 4 /pyridine, 10 etc. Many of these reagents lack generality for oxidation of alcohols, benzoins and hydrobenzoins, besides being expensive, and giving low yields and undesirable side products.…”

Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

“…[1][2][3][4][5] As for the application of trivalent organoantimony compounds (stibanes), a wide variety of reactions such as self-coupling reactions, 6,7) cross-coupling reactions, [8][9][10][11][12][13] photoreaction, 14) and asymmetric reactions with optically active organoantimony compounds [15][16][17][18][19] have been reported during the last two decades. On the other hand, the conversion of benzoin into benzil has been accomplished by oxidation with a variety of reagents; i.e., bismuthane oxide, 20) bismuthane imides, 21) alumina-supported copper sulfate under microwave irradiation, 22) and the Burgess reagent, 23) and by transition metal-catalyzed oxidation with bismuth nitrate-copper acetate, 24) aerobic oxygen, 25,26) diacetoxyiodobenzene, 27) and allyl diethyl phosphate. 28) In this respect, pentavalent antimony compounds such as stibane oxide, 20) diacetoxytriphenystiborane, 29) dibromotriphenylstiborane, 30,31) and stibane imides 21) were also known to be effective for this reaction.…”