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Beilstein J. Org. Chem. 2011, 7, 1663–1670, doi:10.3762/bjoc.7.196
Graphical Abstract
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).