Issue 0, 1986

Photochemistry of substituted cyclic enones. Part 5. 3-Aryl-5-(3-phenylprop-2-enyl)cyclopent-2-enones

Abstract

The E- and Z- compounds (1) and (2; Ar = Ph, 4-MeOC6H4, and 4-NCC6H4), were synthesised by standard procedures. The E- and Z-isomers set up a rapid photochemical equilibrium prior to formation of tricyclic [2 + 2]-cycloaddition products, 6-aryl-4-exo- and endo-phenyltricyclo[3.2.1.03,6]octan-2-ones, (3) and (4) respectively. The exo-tricyclic ketones (3) undergo further photolysis to afford the cyclobutanecarbaldehydes (6), which rearrange thermally to the enol ethers (7). The 6-endo-phenyl isomers (4) do not photolyse further. Boron trifluoride-assisted rearrangement of compounds (4) affords the cyclohexanones (9) and, in the case of the 4-cyanophenyl compound, the cyclohexenone (10c). Similar rearrangement of compound (3b) affords the ketone (8b), but compound (3c) gives no corresponding ketone (8c) but rather, traces of the monocycle (1c).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 1235-1242

Photochemistry of substituted cyclic enones. Part 5. 3-Aryl-5-(3-phenylprop-2-enyl)cyclopent-2-enones

I. D. Cunningham, T. B. H. McMurry, M. P. Napier and S. N. Rao, J. Chem. Soc., Perkin Trans. 1, 1986, 1235 DOI: 10.1039/P19860001235

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