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Mechanistic studies in the photochemical fries rearrangement of enol esters
Year:
1980
Authors :
Veierov, Dan
;
.
Volume :
Co-Authors:
Veierov, D., 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:
1659
To page:
1664
(
Total pages:
6
)
Abstract:
Photolysis of several enol esters produces the corresponding 1,3-Fries products, i.e. the keto forms of the β-diketones, as the sole primary photoproducts. The quantum yields of the rearrangements under a variety of conditions were measured. They decrease when the number of fused aromatic rings in the acyl part of the molecules is increased. The photobehaviour of the 2-anthroyl derivative is exceptional, in being affected both by the exciting wavelength and the solvent. Its irradiation at 254 nm results in a photo-Fries rearrangement (p.f.r.) with a yield twice that in ethanol; irradiation at 366 nm causes only inefficient dimerization. Explanations are forwarded for the general photobehaviour of the enol esters and its relation to the 1,3-p.f.r. of aryl esters and to other photoinduced 1,3-shifts.
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DOI :
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Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
29188
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:44
Scientific Publication
Mechanistic studies in the photochemical fries rearrangement of enol esters
Veierov, D., 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
Mechanistic studies in the photochemical fries rearrangement of enol esters
Photolysis of several enol esters produces the corresponding 1,3-Fries products, i.e. the keto forms of the β-diketones, as the sole primary photoproducts. The quantum yields of the rearrangements under a variety of conditions were measured. They decrease when the number of fused aromatic rings in the acyl part of the molecules is increased. The photobehaviour of the 2-anthroyl derivative is exceptional, in being affected both by the exciting wavelength and the solvent. Its irradiation at 254 nm results in a photo-Fries rearrangement (p.f.r.) with a yield twice that in ethanol; irradiation at 366 nm causes only inefficient dimerization. Explanations are forwarded for the general photobehaviour of the enol esters and its relation to the 1,3-p.f.r. of aryl esters and to other photoinduced 1,3-shifts.
Scientific Publication
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