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.

Paper | Regular issue | Vol 83, No. 4, 2011, pp.789-796
Published online, 22nd February, 2011
DOI: 10.3987/COM-11-12135
Synthesis and Emission Properties of 1,6-Methano[10]annulene-3,4-dicarboximides

Shigeyasu Kuroda,* Naoko Tamura, Ryuta Miyatake, Naoko Matsumoto, Yoshikazu Horino, Daisuke Miyawaki, and Mitsunori Oda*

*Department of Environmental Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan


A mixture of 1,6-methano[10]annulene-3,4-dicarboximide (1e) and 1,6-methano[10]annulene-3,4-dicarboxylic anhydride (3) was obtained through a two-step sequence involving cyanation and subsequent hydrolysis from ethyl 4-bromo-1,6-methano[10]annulene-3-carboxylate (5). Alkylations of 1e provided 1f and 1g, and the nucleophilic substitution of p-fluoronitrobenzene with 1e yielded 1i. Copper-catalyzed arylations of 1e with arylhalides gave 1a and 1h. Reactions of 3 with anilines afforded 1a and 1h. Emission properties of the imides obtained are also reported.