Electrochemical methoxylation of acenaphthylene. A stereoselective effect of anode material

Electrochemical reactions of alkenes induced by anodic oxidation and their applications in organic synthesis

“…The optimal conditions for these reactions are as follows: the initial concentration of alkene >1 mol litre 71 , methanol as the solvent, NaClO 4 as the supporting electrolyte, and a graphite anode. 33,35,38,72 Under these conditions, the aliphatic and alicyclic vinyl ethers 41, 42 are converted into ketals of 1,4-dicarbonyl compounds, which are hydrolysed to give the corresponding diketones; 5,6-dihydro-4-pyran ( 43) is converted into dimethoxy derivative 44.…”

“…Two Note. Electrolysis was carried out under potentiostatic conditions in an undivided cell (PCU) with a graphite anode; the current yield was determined relative to the isolated products; the initial concentration of the substrate was 5.8 ± 6.0 mol litre 71 .…”

“…The process selectivity sharply decreases when the initial alkene concentration is higher than 1.0 mol litre 71 because of the increase in the relative amount of the alkene involved in the side dimerisation, oligomerisation and polymerisation reactions (see Section II.5). The decrease in the alkene concentration in the reaction mixture by using its gradual addition to the electrolyte during electrolysis makes it possible to increase the product yield to 15% ± 20%.…”

“…In this review, we consider later publications. n = 1, 2; R 1 , R 2 = H, Me, Pr i ; (a) ACU, Pt anode, 4 F mol 71 , MeOH ± AcOH (10 : 1), LiClO4, 2 ± 8 8C.…”

“…170 ± 172 The reaction is carried out in an undivided cell (at *20 8C) in acetic acid with Et 4 NOTs as the supporting electrolyte in the presence of 2 ± 4 equiv. of benzenethiol with passage of 20 mA current for 1-min periods at 30-min intervals (0.16 ± 1.19 F mol 71 ) and with bubbling oxygen.…”