Rybalkin Vladimir P, Zmeeva Sofiya Yu, Popova Lidiya L, Tkachev Valerii V, Utenyshev Andrey N, Karlutova Olga Yu, Dubonosov Alexander D, Bren Vladimir A, Aldoshin Sergey M, Minkin Vladimir I
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, Rostov on Don 344006, Russian Federation.
Institute of Physical and Organic Chemistry, Southern Federal University, Rostov on Don 344090, Russian Federation.
Beilstein J Org Chem. 2020 Jul 22;16:1820-1829. doi: 10.3762/bjoc.16.149. eCollection 2020.
2-Benzo[]thienyl fulgides and fulgimides containing bulky diphenylmethylene substituents were synthesized in the form of their ring-opened - or 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 - and isomers and of products of the photoinduced rearrangement completed by 1,5-H shift reaction, 3a,4-dihydronaphtho[2,3-]furans(pyrroles) , were established based on the data of H and C NMR spectroscopy and X-ray diffraction studies.
