Synthesis of Cis/trans-dihydrochromenones via Photoinduced Rearrangement of 4-Phenyl-3-aryl/cyclohexenylcoumarins

A concise and environmental friendly protocol has been developed for the synthesis of cis-dihydrochromenones and trans-dihydrochromenones in EtOH at room temperature. Irradiation of 4-phenyl-3-arylcoumarins with a 313 nm UV light...

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

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.

Synthesis of substituted naphtho[1,2-b]benzofuran-7(8H)-ones via photoinduced rearrangement of 4H-chromen-4-one derivatives

A simple and efficient method was developed for the synthesis of substituted naphtho[1,2-b]benzofuran-7(8H)-ones based on the photorearrangement reaction of 4H-chromen-4-one derivatives.

Photoinduced rearrangement of vinyl tosylates to β-ketosulfones

We developed a photoinduced radical fragmentation and rearrangement of vinyl tosylates that enables efficient formation of β-ketosulfones.