Journal of the Chemical Society. Perkin transactions I p. 529 - 535 (1996)
Update date:2022-08-05
Topics:
Kohmoto, Shigeo
Kobayashi, Takashi
Nishio, Takehiko
Iida, Ikuo
Kishikawa, Keiki
Yamamoto, Makoto
Yamada, Kazutoshi
The photocyclisation of N-cinnamoyl-1-naphthamides 1a-f was examined in the solid state and in solution. Three types of cyclisation, intramolecular 2π + 2π and 4π + 2π, and intermolecular 2π + 2π cyclisations were observed in the solid state. The ratios of these products were largely dependent on the substituents at the para-position of the cinnamoyl moiety. Single-crystal X-ray crystallographic analysis of 1b showed that the intermolecular distance between the two double bonds was 4.34 A. Amides with bulky substituents preferred intramolecular 2π + 2π cyclisation. In contrast to the solid-state photochemistry, only intramolecular cyclisation was observed in solution. The ratios of 2π + 2π and 4π + 2π cyclisation products were irradiation time dependent. It was found that the 2π + 2π cycloreversion and rearrangement from the 2π + 2π product to the endo 4π + 2π isomer were the cause of this dependency.
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