A selective conversion of benzilic alcohols to the corresponding carbonyl compounds by means of an Ag(III) and Cu(III) complexes

Abstract

The oxidation of alcohols into aldehydes and ketones is a ubiquitous transformation in organic chemistry and numerous oxidizing agents are available to effect this key reaction. This reaction raises continuous interest, but most of these reactions have not been applied to sensitive natural polyfunctional products. In recent years investigators have been increasingly interested in studies of unusual oxidation states of transition metals such as Cu(III), Ni(III), Ni(IV), Ag(III). We now have looked more closely at the possibility of preparing carbonyl compounds with the aid of Ag(III) and Cu(III) complexes, partly because it is unusual for Ag and Cu species to have charge +3, which means it can easily change charge; partly because complex being easily made of inexpensive chemicals.1,2 Investigations have been carried out with some potentially oxidable substrates which contains different type of hydroxyl group in the molecule like D-(-)-threo-2-dichloroacetamido-1-(4- -nitrophenyl)-1,3-propanediol(chloramphenicol), (1R,2R)-(-)-2-amino-1-(4-nitrophenyl)-1, 3 -propanediol, (S)-1 phenyl- 1, 3 -propanediol and Ag(III) and Cu(III) complexes. The method gives the possibility of selective oxidation of benzylic hydroxyl groups in polyhydroxyl compounds in good yields. Such systems occur in nature and medicine and thus there is considerable interest in devising synthetic methods for their regioselective oxidation.