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• W2009213508 abstract "Following our previous reports on the spectroscopy and photochemistry of methyl ethers of cyclic α-oxo oximes, we have now studied a number of o- and p-benzoquinone mono-oxime O-methyl ethers and, for comparison, some corresponding o- and p-benzoquinones. The ground-state electronic structure of o-benzoquinones is described satisfactorily by the sum of the two propenal fragments. The structure of the corresponding (E)- and (Z)-mono-oxime ethers can be described similarly as the sum of the propenal and (E)- or (Z)-(methoxyimino)propene fragments. This method fails when used for the construction of the ground-state electronic structure of the isomeric p-benzoquinones and their mono-oxime ethers.The UV spectra of o-benzoquinone mono-oxime ethers are quite different from those of the parent o-benzoquinones in that the free lying n+ π* absorption of the latter is, for the former, shifted to lower wavelength and apparently hidden under the long-wavelength ππ* absorptions. For the p-benzoquinone mono-oxime O-methyl ether 12, however, the long-wavelength nπ* absorption remains visible.Direct irradiation of the tert-butyl-substituted o-benzoquinone mono-oxime O-methyl ethers (E)-5–(E)-7 dissolved in acetonitrile at λ 350 nm leads (in addition to E-Z isomerization) to the formation of the (E)-azobenzenes 16–19 by dimerization of the respective phenylnitrenes. However, in addition, the 2,4-di-tert-butyl derivative (E)-7 undergoes mainly γ-hydrogen abstraction, probably from the S1(nπ*) state, leading to subsequent cyclization to the relatively stable dienol (E)-14, which eventually isomerizes thermally to the enone (E)-15. Evidence is presented that (Z)-7 exhibits only Z-E photoisomerization and no photocyclization, as has been observed previously with the saturated six-membered ring analogue. Direct irradiation of the corresponding 3,5-di-tert-butyl-o-benzoquinone (3) at 350 nm leads to decarbonylation with formation of cyclopentadienone 13. Sensitized irradiation of mono-oxime O-methyl ether (E)-7, using 1-acetylnaphthalene and 1-fluorenone as triplet sensitizers and acetonitrile as solvent, leads to E-Z isomerization only with eventual photo-stationary state [E]/[Z] ratios of 0.78 and 0.88, respectively.The p-benzoquinone mono-oxime O-methyl ethers 11 and 12 are photostable against 254, 300 and 350 nm radiation; however, any occurring E-Z isomerization escapes detection for symmetry arguments." @default.
• W2009213508 created "2016-06-24" @default.
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• W2009213508 date "2010-09-02" @default.
• W2009213508 modified "2023-09-25" @default.
• W2009213508 title "Spectroscopy and photochemistry of a series of alkyl-substituted o- and p-benzoquinones and their mono-oxime O-methyl ethers" @default.
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• W2009213508 doi "https://doi.org/10.1002/recl.19921111005" @default.
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