Radical anions produced by electrochemical reduction of 1,3-diketones

Electrolytic reductive coupling of 1,3-diphenyl-1,3-propanedione and derivatives

“…After a number of recrystallizations, a small amount of product, mp 205-210 °C, was obtained. This was identified as a mixture of 2f and an isomer of 6f: NMR of mixture 2.00 (s, OH), 2.21 (s, CH3), 2.26 (s, CH3), 2.36 (s, CH3), 2.40 (s, CH3), 2.52, 2.70, 4.22, 4.41 (AB, CH2 (open chain), Jab = 18.5 Hz), 3.01,3.17,3.29,3.44 [AB, CH2 (cyclized), Jab = 15.5], 4.26 (s, OH), 5.27, (s, CH), 5.33, (s, OH), 6.03 (s, OH), 6.83-7.32, 7.50-7.92 (m, arom). The singlets at 2.00, 4.26, 5.33, and 6.03 disappear on addition of D20.…”

Electrochemical oxidation of the enolate of dibenzoylmethane

“…21.22 The 2,2-dimethyl-l,3-diphenyl-l,3-propanedione was prepared earlier. 23 Solutions were deaerated with nitrogen. The solution temperature was 24 ± 1 °for all electrochemical experiments.…”

Electrochemical reduction of 1,3-diketones in hydroorganic medium. Preparation of 1,2-cyclopropanediols

“…Preparative electrolysis carried out at pH 3.7 with 400 mg of 11 gives an oil. The nmr spectrum and the easy oxidation into 11 indicate a mixture of the isoluers of 1,3-dimethyl-2-phenyl-3-benzyl-1,2-cyclopropanediol 12 [8] that this compound behaves as an a-diketone (reduction into an enediol followed by a rearrangement into an a-ketol). This is not surprising as this compound is a vinylogue of a-diketone.…”

“…l-Phenyl-2-methyl-l,3-butanedione, 8 Between p H 1 and 8, compound 8, C6H5-CO-CH(CH3)-CO-CH3, shows a p H dependent 2e wave (C = M, 50y0 CH30H).…”