Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

• Main Authors: Vladimir P. Rybalkin, Sofiya Yu. Zmeeva, Lidiya L. Popova, Valerii V. Tkachev, Andrey N. Utenyshev, Olga Yu. Karlutova, Alexander D. Dubonosov, Vladimir A. Bren, Sergey M. Aldoshin, Vladimir I. Minkin
• Format: Article
• Language: English
• Published: Beilstein-Institut 2020-07-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: benzo[b]thiophene; fulgide; fulgimide; photorearrangement; x-ray diffraction
• Online Access: https://doi.org/10.3762/bjoc.16.149

2-Benzo[b]thienyl fulgides and fulgimides containing bulky diphenylmethylene substituents were synthesized in the form of their ring-opened E- or Z-isomers. In contrast to the majority of known fulgides/fulgimides, that form colored ring-closed structures under UV irradiation, the obtained compounds undergo an irreversible transformation leading to decoloration of their solutions. This rearrangement with the formation of the dihydronaphthalene core appeared to be by 2–3 orders of magnitude more efficient than for the known diphenylmethylene(aryl(hetaryl))fulgides. The molecular structures of E- and Z-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.