Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.