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.

Communication | Regular issue | Vol 26, No. 9, 1987, pp.2365-2368
Published online, 1st January, 1970
DOI: 10.3987/R-1987-09-2365
First Stable Selenabenzene Analogue, 2-Cyano-1-methyl-4-phenyl-1-selenanaphthalene: Synthesis and Reactions

Mikio Hori, Tadashi Kataoka, Hiroshi Shimizu, Kazuhiro Tsutsumi, and Shinya Imaoka

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


2-Cyano-1-methyl-4-phenyl-1-selenanaphthalene (1) was synthesized as the first isolable selenabenzene. Its ylidic structure was characterized by the spectral and chemical evidence. The thermal reaction of the selenanaphthalene 1 afforded [1,2]- (5) and [1,4]-rearranged products (6) together with dimeric compounds 7. The photochemical reaction afforded the different [1,4]-rearranged product, ketenimine 9 and the photo-oxygenated product, 4-phenylcoumarin (10).