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 | Special issue | Vol 11, No. 1, 1978, pp.113-120
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0113
7-Azanorbornadiene — 3-Azaquadricyclane

Horst Prinzbach* and Horst Babsch

*Chemusches Laboratorium, Universität Freiburg, Albertstr. 21, D-7800 Freiburg, Germany


A synthesis for the C-unsubstituted 7-azanorbornadiene skeleton (9) has been devised. Its transformation to the 3-azaquadricyclane (10) by sensitised photoexcitation is uniform and quantitative. The latter can, without any competition, be thermally isomerised into the N-tosylazepine (11). The clear preference for this [4+2]-cycloreversion reaction via the ylid (17) can be understood on the basis of the kinetic data.