159149-14-1Relevant academic research and scientific papers
1,3-Dipolar cycloadditions of photoinduced carbonyl ylides. Part 2. Photoreactions of α,β-unsaturated γ,δ-epoxy dinitriles and ethyl vinyl ether
Kotera, Masashi,Ishii, Keitaro,Tamura, Osamu,Sakamoto, Masanori
, p. 313 - 318 (1998)
Photoinduced carbonyl ylides B, C, E and F from the α,β-unsaturated γ,δ-epoxy dinitriles 2,3,5 and 6, respectively, undergo 1,3-dipolar cycloaddition with ethyl vinyl ether, leading to the tetrahydrofuran system. The cycloaddition proceeds with high regioselectivity affording predominantly the exo-adduct. However, the ylide from the mononitrile 1 and dinitrile 4 gives little or no adduct. The observed regioselectivity and the difference of the reactivity in these cycloadditions can be nicely accommodated in terms of semiempirical AMI calculations. The reactivity of the cycloaddition depends on the LUMO energy level and the C(γ),C(δ) distance of the ylide.
1,3-Dipolar Cycloadditions of Photoinduced Carbonyl Ylides from α,β-Unsaturated γ,δ-Epoxy Dinitriles
Kotera, Masashi,Ishii, Keitaro,Tamura, Osamu,Sakamoto, Masanori
, p. 2353 - 2354 (2007/10/02)
The photoinduced carbonyl ylides B and C from the α,β-unsaturated γ,δ-epoxy dinitriles 2 and 3 indergo 1,3-dipolar cycloaddition with enol ethers, leading regioselectively to the 8-oxabicyclooctane system.
