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 34, No. 12, 1992, pp.2339-2348
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6158
Formations of 1,1’-Biazaazulanones through [8+2]-Type Cycloaddition Reactions of Tropone Azine with Heterocumulenes

Kazuaki Ito, Katsuhiro Saito,* and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466, Japan


Reaction of N-aryl-2,4,6-cycloheptatrien-1-imine with hydrazine afforded tropone azine, which reacted with chloroketenes to give 1,1’-biazaazulanones via [8+2]-type cycloadducts followed by elimination of hydrochloride. The similar reaction using phenyl isocyanate afforded a [8+2]-type 1:2 cycloadduct, while the reaction with phenyl isothiocyanate yielded only a 1:1 cycloadduct. 15N and 13C nmr spectra on C=N bond of tropne azine showed a minor contribution of a dipolar structure compared with the case of N-aryl-2,4,6-cycloheptatrien-1-imines.