Abstract
Depending on the multiplicity of the excited state, alternative photoreactions are realized in methoxy and acetoxy derivatives of aldonitrone vinylogs: diabatic nitrone-oxazypyridone rearrangement in the first excited singlet state and E-Z isomerization involving the C=N bond in the triplet state. In the case of aldonitrone vinylogs with an o-hydroxy group in the α-aryl ring one observed adiabatic proton transfer from the hydroxy group to the azotoxido group with a subsequent diabatic reaction involving cyclization to the 2H-chromene structure. The same transfer is also realized in the triplet state. The quantum yields were determined, and the energies of activation of the photoreactions and the reverse thermal processes were evaluated.
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A. V. Metelitsa, O. T. Lyashik, N. V. Volbushko, I. M. Andreeva, M. I. Knyazhanskii, E. A. Medyantseva, and V. I. Minkin, Zh. Org. Khim., 22, 1446 (1986).
A. Albini and M. Alpegiani, Chem. Rev., 84, 43 (1984).
K. Koyano and I. Tanaka, J. Phys. Chem., 69, 2545 (1965).
L. Bellamy, New Data on the IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971).
N. Harada, Y. Mori, and I. Tanaka, Mol. Photochem., 2, 153 (1970).
H. Gorner and D. Shulte-Frohlide, J. Mol. Struct., 84, 227 (1982).
D. Calvert and D. Pitts, Photochemistry [Russian translation], Mir, Moscow (1968).
D. Baltrop and D. Coyle, Excited States in Organic Chemistry [Russian translation], Mir, Moscow (1978).
B. M. Krasovitskii and B. M. Bolotin, Organic Luminophores [in Russian], Khimiya, Leningrad (1976).
A. Gordon and R. Ford, The Chemist's Guide [Russian translation], Mir, Moscow (1976).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1373–1378, October, 1990.
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Metelitsa, A.V., Knyazhanskii, M.I., Volbushko, N.V. et al. Energetics and structural mechanisms of photochemical processes in molecules of aldonitrone vinylogs. Chem Heterocycl Compd 26, 1145–1149 (1990). https://doi.org/10.1007/BF00472188
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DOI: https://doi.org/10.1007/BF00472188