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Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study

1996; Issue: 12 Linguagem: Inglês

10.1039/p19960001487

2050-8255

Vijay Nair, Jessy Mathew, K. V. Radhakrishnan,

Radical Photochemical Reactions

The oxidative addition of dimedone, acetylacetone and ethyl acetoacetate to cyclic and acyclic alkenes mediated by CAN gives dihydrofurans in good yields. Similar addition of the radical generated from dimethyl malonate to alkenes provides lactones. A comparative study of these reactions vis-à-vis those mediated by Mn(OAc)3 has shown that the former generally lead to higher yields of products. The milder reaction conditions, experimental simplicity, and the solubility of CAN in common organic solvents like methanol, acetonitrile and THF are other advantages. Thus it appears from this study that CAN is superior to the commonly used Mn(OAc)3.