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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.
Beilstein J. Org. Chem. 2011, 7, 1663–1670, doi:10.3762/bjoc.7.196
Figure 1: Resonance structures of the sydnone ring.
Scheme 1: Thermal and photochemical intermolecular [3 + 2] cycloadditions.
Figure 2: Illustration of intramolecular [3 + 2] cycloadditions.
Figure 3: Styryl-sydnone 1 and stilbenyl sydnone 2 and their photoproducts F and G, respectively; target mole...
Scheme 2: Synthesis of the target molecules 3a and 3b.
Scheme 3: Photolysis of cis- or trans-3.
Scheme 4: Aromatization with DDQ.
Scheme 5: Possible mechanism for the formation of the photoproducts.
Scheme 6: Thermal reaction of trans-3.
Figure 4: ORTEP of compound 14.
Scheme 7: Thermal reaction of cis-3.
Figure 5: Proposed stereochemical pathway of sydnone ring (CH–N) and trans- and cis-stilbene (α–β).
Figure 6: Proposed stereochemical pathway of sydnone ring (N–CH) and trans- and cis-stilbene (α–β).
Scheme 8: Possible formation of thermal products 14 (from trans-3) and 15 (from cis-3).