94800-16-5Relevant academic research and scientific papers
Manganese(III)-Mediated Spirodilactonization
Fristad, William E.,Hershberger, Susan S.
, p. 1026 - 1031 (1985)
Manganese(III) oxidation of malonic acid in the presence of alkenes results in the formation of spiro-fused lactones, 2,7-dioxaspirononane-1,6-diones.Terminal alkenes produce a mixture of the three possible diastereomers.The stereochemistry of the diastereomeric spirodilactones was determined by NMR and corroborated by the intensity of the coupled IR carbonyl stretching frequencies. 1,1,6,6-Tetrasubstituted 1,5-hexadienes give in one step tricyclic dilactones.Mechanistic and synthetic aspects of this reaction are discussed.
