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
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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