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Effect of additives and solvents on the fate of the primary photoproduct of 1,3-dicarbonyl compounds
Year:
1978
Source of publication :
Journal of Organic Chemistry
Authors :
Veierov, Dan
;
.
Volume :
43
Co-Authors:
Veierov, D., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel, Feinberg Graduate School, Weizmann Institute of Science, Rehovot, Israel
Bercovici, T., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Mazur, Y., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Fischer, E., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Facilitators :
From page:
2006
To page:
2010
(
Total pages:
5
)
Abstract:
The primary photoproduct of the chelated enol tautomer of the title compounds is a nonchelated enol. Primary and tertiary amines added at up to equimolar concentrations greatly enhance the rate of the secondary thermal reactions, i.e., re-formation of the chelated enol, and tautomerization to the diketone. Triethylamine enhances the quantum yield of photoketonization. Ethanol added at up to 0.5 M concentrations also enhances the rate of the thermal re-formation of the starting compound. Differences between the solvents hexane, cyclohexane, benzene, and acetonitrile are marginal. It is suggested that the unchelated enol transient undergoes efficient formation of a complex with the amines and, to a much smaller extent, with ethanol. The rates of the spontaneous reactions of these complexes differ greatly from those of the free transient. © 1978 American Chemical Society.
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DOI :
Article number:
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Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
29003
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:43
Scientific Publication
Effect of additives and solvents on the fate of the primary photoproduct of 1,3-dicarbonyl compounds
43
Veierov, D., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel, Feinberg Graduate School, Weizmann Institute of Science, Rehovot, Israel
Bercovici, T., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Mazur, Y., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Fischer, E., Departments of Organic and Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Effect of additives and solvents on the fate of the primary photoproduct of 1,3-dicarbonyl compounds
The primary photoproduct of the chelated enol tautomer of the title compounds is a nonchelated enol. Primary and tertiary amines added at up to equimolar concentrations greatly enhance the rate of the secondary thermal reactions, i.e., re-formation of the chelated enol, and tautomerization to the diketone. Triethylamine enhances the quantum yield of photoketonization. Ethanol added at up to 0.5 M concentrations also enhances the rate of the thermal re-formation of the starting compound. Differences between the solvents hexane, cyclohexane, benzene, and acetonitrile are marginal. It is suggested that the unchelated enol transient undergoes efficient formation of a complex with the amines and, to a much smaller extent, with ethanol. The rates of the spontaneous reactions of these complexes differ greatly from those of the free transient. © 1978 American Chemical Society.
Scientific Publication
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