915775-49-4Relevant academic research and scientific papers
Photochemical reactions of 1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2- ones
Chang, Shi-Yi,Huang, Shih-Lin,Villarante, Nelson R.,Liao, Chun-Chen
, p. 4648 - 4657 (2006)
The photochemistry of 1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2-ones 1a-f containing multiple chromophoric moieties under various conditions is described. Upon direct irradiation, dienones 1a-f in benzene, acetonitrile, and methanol were found to aromatize through photoelimination of dimethylketene, which was trapped with 3-phenylprop-2-en-1-ol (12). Triplet sensitization of dienone 1a in acetone and in acetone/acetophenone mixed solvents afforded aromatic compound 2a, whilst bicyclic systems 1b-c were found to be unreactive on sensitization. In the cases of dienones 1d-f in acetone, aromatic compounds 2d-f and di-π-methane (DPM) photoproducts 3d-f and 4f were observed, but in the acetone/acetophenone mixed solvent system only DPM photoproducts were detected. Plausible mechanisms for these photochemical reactions are described. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
