Change of selectivity in the photo-Fries rearrangement of phenyl acetate induced by .beta.-cyclodextrin
โ Scribed by Veglia, Alicia V.; Sanchez, Ana M.; De Rossi, Rita H.
- Book ID
- 126951946
- Publisher
- American Chemical Society
- Year
- 1990
- Tongue
- English
- Weight
- 530 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0022-3263
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๐ SIMILAR VOLUMES
## Cyclodextrin encapsulation, both in the solid state and in aqueous solution brings about a remarkable regulation of the photo-Fries rearrangement of phenyl esters and anilides. In comparison to the nonselective mixture of ortho and para-rearranged isomers along with the deacylated product obta
The Fries rearrangement of phenyl acetate is catalysed by acidic zeolites such as H-Nu-2 and H-ZSM-5, with selectivities of 2-6:l in favout of para-substituted products. The Fries rearrangement of phenyl esters affords a mixture of o-and phydroxyphenylketones, together with phenol as a hydrolysis p
The rate constants for the 1,3-and 1,Mgmatropic hydrogen shifts of the phot&Fries rearranged intermediates of phenyl acetate produced by laser flash photolysis at 266 nm were directly measured in several solvents. The rate constant for the 1,3hydrogen shift (3.6 s-l) was faster than that for the l&s