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Note | Regular issue | Vol 51, No. 9, 1999, pp.2147-2157
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8570
1,3-Dipolar Cycloadditions of Photoinduced Carbonyl Ylides. Part 3: Photoreactions of α,β-Unsaturated γ,δ-Epoxy Dinitrile, α-Cyano Ester, and Diester with Various Dipolarophiles

Masashi Kotera, Keitaro Ishii,* Masaru Hiraga, and Masanori Sakamoto

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

Photoinduced carbonyl ylide (A) from α,β-unsaturated γ,δ-epoxy dinitrile (1) undergoes 1,3-dipolar cycloaddition with enol ethers, leading to tetrahydrofuran system with high regioselectivity in moderate yield. However, The cycloadditions of A with nonactivated and electron-deficient olefins and with C=N containing dipolarophiles gave the corresponding adducts slightly. The reactivity for the cy-cloaddition of α-cyano ester (8) and diester (9) with ethyl vinyl ether decreases.