Conclusions
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1.
We were the first to identify the oxidation product of 1-ethoxy-2-ethylthioethene as being the diethyl monothioacetal of glyoxal; it proved that the dark oxidation of 1-ethoxy-2-ethylthioethene with molecular oxygen to glyoxal diethyl monothioacetal is possible only for the cis-isomer.
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2.
A method was developed for the photochemical oxidation of the trans-isomer of 1-ethoxy-2-ethylthioethene, adsorbed on porous glass, to the diethyl monothioacetal.
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3.
Based on the kinetic and stereochemical characteristics of the reaction, a mechanism was proposed for the oxidation process, which includes the formation of an intermediate complex from two molecules of the oxidized substrate and one molecule of oxygen.
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4.
It was established by the EPR method that the O −2 ion-radical is formed in the photochemical oxidation of trans-1-ethoxy-2-ethylthioethene, which takes part in the oxidation process.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1139–1146, May, 1975.
The authors express their deep gratitude to V. A. Shvets for his interest in. the work and for taking part in a discussion of the obtained results, and also to M. L. Mironova for supplying the porous glass samples.
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Shekhtman, R.I., Krongauz, V.A., Borovkov, V.Y. et al. Dark and photochemical oxidation reaction of 1-ethoxy-2-ethylthioethene stereoisomers. Russ Chem Bull 24, 1046–1052 (1975). https://doi.org/10.1007/BF00922962
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DOI: https://doi.org/10.1007/BF00922962