Beilstein J. Org. Chem.2020,16, 1820–1829, doi:10.3762/bjoc.16.149
-isomers and of products of the photoinduced rearrangement completed by 1,5-H shift reaction, 3a,4-dihydronaphtho[2,3-c]furans(pyrroles) C, were established based on the data of 1H and 13C NMR spectroscopy and X-ray diffraction studies.
Keywords: benzo[b]thiophene; fulgide; fulgimide; photorearrangement
the best of our knowledge, this is the first example of an irreversible rearrangement of hetaryl fulgimide into colorless substituted dihydronaphthalene.
Conclusion
To sum up, we report the synthesis of a series of fulgides possessing bulky diphenylmethylene substituents – 3-(diphenylmethylene)-4-((3
) (2.5 × 10−5 M, T = 293 K).
Electronic absorption spectra of fulgimide 8E in acetonitrile solution before (1) and after irradiation with light of 365 nm for 10 (2), 20 (3), 30 (4), 60 (5), 90 (6), 120 (7), 180 (8), 260 (9) and 320 s (10) (2.5 × 10−5 M, T = 293 K).
Photoisomerization of 2-benzo[b]thienyl
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Graphical Abstract
Scheme 1:
Photoisomerization of 2-benzo[b]thienyl fulgides.