Abstract
Resume Sensitized photooxygenation of various 2,5-dialkyl-3,4-diphenyl-cyclopentadie-nones 1 in ether led to the expected (Z)-α,α'-diacylstilbenes 3 uncontaminated by their (E)-isomers. Several of these derivatives, bearing reactive acyl groups, show a special behaviour ; thus with 3c (R1 = R41= Et) an equilibrium takes place in benzene with its cyclic tautomer 11 whereas 3d (R1 = Me, R4= Ph) stays unchanged. Moreover, 3c and 3d add spontaneously primary alcools to give the dihydrofuranic diacetals 8 and 9 . Under acid catalysis, the reaction goes further up to the furanic ethers 12 and 18 (with CH3OH) snd even to the vinylfuran 13 with 3c or 8c . (E)-α,α'-diacylstilbenes 4c,d have been obtained by photochemical isomerizatlon of their (Z)-isomers ; they do not add spontaneously alcohols.
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