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Photochemical formal [4π + 2π + 2π] cycloreversion of 7,8‐diaza‐3‐oxatricyclo[4.2.10 2,5 ]non‐7‐enes
Author(s) -
Kohmoto Shigeo,
Kishikawa Keiki,
Yamamoto Makoto,
Yamada Kazutoshi
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610081206
Subject(s) - benzophenone , chemistry , photodissociation , photochemistry , thermal decomposition , decomposition , organic chemistry
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 [4π + 2π + 2π] cycloreversion in a formal way, the first example in azoalkane chemistry. This cycloreversion was found to be sensitized by the benzophenone produced. In contrast, thermolysis showed the typical decomposition pattern of azoalkanes, extrusion of nitrogen and subsequent σ‐bond formation of the resulting biradical to afford the tricyclic oxetanes