Oxidation Riley

Oxidation a to a carbonyl group is called a Riley oxidation. 

The selectivity was useful in a synthesis of nojigku alcohol (8) from (—)-isobornyl acetate (4). Oxidation of 4 with CrOj gave a mixture of 5 and 6, which was converted into 7 in high yield by Riley oxidation and reduction. The conversion of 7 into 8 involves elimination of the 5-keto group and Wagner-Meerwein rearrangement. ... 

In the laboratory of T.-J. Lu, a highly stereoselective method for the asymmetric synthesis of a-amino acids was developed by the alkylation of a chiral tricyclic iminolactone derived from (+)-camphor. The iminolactone can be considered a glycine equivalent. The synthesis commenced with the Riley oxidation of (+)-camphor to obtain the corresponding (+)-camphorquinone. Amino acids are obtained by first alkylating the a-position of the lactone with various alkyl halides and then hydrolyzing the monosubstituted products. The advantage of this technique was that the chiral auxiliary could be fully recovered without the loss of any optical activity. 

Riley oxidations. Oxidations of organic compounds with selenium dioxide, e.g., the oxidation of active methylene groups to carbonyl groups. 

Other references related to the Riley oxidation are cited in the literature. ... 

Sol 4. (i) Se02 oxidizes active methylene or methyl group present adjacent to the carbonyl group to give 1,2-dicarbonyl compounds. This reaction is called Riley oxidation. 

This reaction is sometimes referred to as the Riley oxidation. We may start writing the mechanism in much the same manner as for allylic oxidation, with the carbonyl group taking the place of the carbon-carbon double bond ... 

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