100374-57-0Relevant academic research and scientific papers
Substituent effects on the 4π + 2π cycloadditions of 4H-pyran-4-one derivatives
Rudas, Monika,Fejes, Imre,Nyerges, Miklos,Szoelloesy, Aron,Toke, Laszlo,Groundwater, Paul W.
, p. 1167 - 1172 (1999)
The simple y-pyranones 4,5, and 6 undergo 4π + 2π cycloaddition reactions with Danishefsky's diene 8 and azomethine ylides 12,16, and 25 to give a range of cycloadducts. The position of the electron-withdrawing group is the decisive factor in these reactions, with the 2-substituted derivatives 5 and 6 being less reactive than the 3-substituted γ-pyranone 4. The esters, 4 and 5, react via addition across the 2,3-C=C bond of the pyranone ring, whilst the aldehyde 6 reacts via addition across the C=O of the carbaldehyde group.
