PHOTOCHEMICAL FORMAL [4-PI-PI+2-PI] CYCLOREVERSION OF 7,8-DIAZA-3-OXATRICYCLO[4.2.1.0(2,5)]NON-7-ENES(2)

Authors
KOHMOTO S KISHIKAWA K YAMAMOTO M YAMADA K
Citation
S. Kohmoto et al., PHOTOCHEMICAL FORMAL [4-PI-PI+2-PI] CYCLOREVERSION OF 7,8-DIAZA-3-OXATRICYCLO[4.2.1.0(2,5)]NON-7-ENES(2), Journal of physical organic chemistry, 8(12), 1995, pp. 799-804
Citations number
23
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of physical organic chemistry → ACNP
ISSN journal
08943230
Volume
8
Issue
12
Year of publication
1995
Pages
799 - 804
Database
ISI
SICI code
0894-3230(1995)8:12<799:PF[CO7>2.0.ZU;2-J
Abstract
The photolysis and thermolysis of 7,8-diaza-3-oxatricyclo[4.2.1.0(2,5) ]non-7-enes were studied. Photolysis showed a novel [4 pi+2 pi+2 pi] c ycloreversion in a formal way, the first example in azoalkane chemistr y. This cycloreversion was found to be sensitized by the benzophenone produced. In contrast, thermolysis showed the typical decomposition pa ttern of azoalkanes, extrusion of nitrogen and subsequent sigma-bond f ormation of the resulting biradical to afford the tricyclic oxetanes.