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Beilstein J. Org. Chem. 2014, 10, 2222–2229, doi:10.3762/bjoc.10.230
Graphical Abstract
Scheme 1: Synthesis of 4- (1) and 5-(2-vinylstyryl)oxazoles (2).
Scheme 2: Irradiation of 4- (1) and 5-(2-vinylstyryl)oxazoles (2) (crude reaction mixtures).
Figure 1: Part of 1H NMR spectra in C6D6 of the crude photomixtures after 200 min (300 nm, rt ) of irradiatio...
Scheme 3: Plausible mechanisms of oxazoline ring-opening in photoproduct 10.
Figure 2: 1H NMR spectra in C6D6 of rel-(9S)-12a (a) and rel-(9S)-11 (b).
Scheme 4: Mechanism of the formation of polycyclic compounds (8–10).
Scheme 5: Reactions of the photochemical product 8 with EtOH, MeOD and H2O/silica gel.
Scheme 6: Plausible mechanisms of oxazoline ring opening in photoproduct 10 and formation of 12.