Tetrahedron p. 339 - 347 (1984)
Update date:2022-08-05
Topics:
Fournier, F.
Berthelot, J.
Pascal, Y. L.
The electrochemical reduction of hindered aromatic ketones which are difficult to reduce alone, can be achieved in an aprotic medium (DMF) on a mercury pool cathode, in presence of Cr(III) chloride, at the reduction potential of the Cr(II)/Cr(0) system, but at a less negative potential than that of the ketone itself.There is a selective hydrodimerisation into an α-glycol, with total lack of polimerisation.With disymmetric ketones, the dl-diastereoisomers of the diols are produced.The effect of chromium is due either to the reduction of a Cr-ketone complex or to thereduction of the ketone by a film of colloidal chromium on the electrode surface.
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