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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

Abstract

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.