V. Nair et al., OXIDATIVE ADDITION OF 1,3-DICARBONYL COMPOUNDS TO ALKENES MEDIATED BYCERIUM(IV) AMMONIUM-NITRATE AND MANGANESE(III) ACETATE - A COMPARATIVE-STUDY, Journal of the Chemical Society. Perkin transactions. I, (12), 1996, pp. 1487-1492
The oxidative addition of dimedone, acetylacetone and ethyl acetoaceta
te to cyclic and acyclic alkenes mediated by CAN gives dihydrofurans i
n good yields, Similar addition of the radical generated from dimethyl
malonate to alkenes provides lactones. A comparative study of these r
eactions vis-a-vis those mediated by Mn(OAc)(3) has shown that the for
mer generally lead to higher yields of products. The milder reaction c
onditions, experimental simplicity, and the solubility of CAN in commo
n organic solvents like methanol, acetonitrile and THF are other advan
tages. Thus it appears from this study that CAN is superior to the com
monly used Mn(OAc)(3).