ELECTROCHEMICAL REDUCTION OF O-ACYLATED ALDEHYDE CYANOHYDRINS

Authors
Citation
Zr. Zheng et H. Lund, ELECTROCHEMICAL REDUCTION OF O-ACYLATED ALDEHYDE CYANOHYDRINS, Journal of electroanalytical chemistry [1992], 441(1-2), 1998, pp. 221-225
Citations number
15
Categorie Soggetti
Electrochemistry,"Chemistry Analytical
Journal title
Journal of electroanalytical chemistry [1992]
ISSN journal
15726657 → ACNP
Volume
441
Issue
1-2
Year of publication
1998
Pages
221 - 225
Database
ISI
SICI code
Abstract
Cyanohydrins of aromatic aldehydes, acylated at the hydroxyl group, ar e reducible in aprotic medium; the base generated during the reduction induces a rearrangement of the compound to a vicinal diketone. Thus, O-benzoyl benzaldehyde cyanohydrin (1) is rearranged during the reduct ion to benzil and O-acetyl benzaldehyde cyanohydrin to 1-phenylpropane -1,2-dione; on the cyclic voltammetric curves of the acylated cyanohyd rins the radical anion of the diketone gives an anodic peak on the rev erse sweep and the diketone a cathodic peak on the second negative swe ep. The reduction of the diketones occurs at a higher potential than t hat of the O-acyl benzaldehyde cyanohydrin and the diketone is therefo re reduced further at the potential used for the reduction of the acyl ated benzaldehyde cyanohydrin. Thus both benzil and O-benzoyl benzalde hyde cyanohydrin yield on reduction the same main product, benzyl phen yl ketone; besides that, 1 gives minor amounts of benzylcyanide and be nzoic acid. Possible reaction routes are discussed. (C) 1998 Elsevier Science S.A.