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Photoreaction of 9-dicyanomethylene-1,2,3,4-tetrahydro-1,4-methanonaphthalene: the 1,3-carbon migrations and the ethylene extrusion to dicyanoisobenzofulvene

✍ Scribed by Noriyuki Tanaka; Tsutomu Kumagai; Toshio Mukai

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 236 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)85437-4

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✦ Synopsis

Irradiation of 9-dicyanomethylene-l,2,3,4-tetrahydro-l,4-methanonaphthalene gave 3,3-dicyano-1,2,3,8b-tetrahydrocyclopent[alindene and 2-dicyanomethylene-2H-indene.

The interaction between two n-functions in excited state has been of interest and much investigated.2 Recently our attention has been given to the interaction induced by dicyanomethylene group in bicyclic system 3 where the 6.9-7.7(88), 'Jl 2= 3.3, J 2,9= 1.0, J2,4= 1.0, J4,5= 6.8 Hz; UV Xmax= 240 (sh, 14300), 286 (sh: 5650), 310 (sh, 3410) nm in acetonitrile. The products 5 and 5 exhibit no dicyano-

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