158. The Fries rearrangement of phenyl laurate and phenyl stearate

Bell, Harold Edwin; Driver, John Edmund

doi:10.1039/jr9400000835

Cited by 7 publications

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“…The presence of significant amounts of POL and Bz 2 indicates that cage‐escape processes compete effectively with in‐cage radical combinations. Somewhat surprisingly and unlike the photoreaction of PPA in hexane, no BzP, a decarboxylation product, was detected (20, 28–45). The lower relative yield of Bz 2 , a combination product of two benzyl radicals from different precursor molecules ( i.e.…”

Section: Resultsmentioning

confidence: 88%

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Comparisons of Photo-Fries Rearrangements of 4-Dodecylphenyl Phenylacetate and Two Structurally Related Esters in Hexane and Polyethylene Cages. How Important Are Anchoring Chains?†

Luo

Passin

Weiss

2006

Photochem Photobiol

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Photo-Fries rearrangements of 4-dodecylphenyl phenylacetate have been investigated in polyethylene films with 0-71% crystallinity and in hexane over a range of temperatures. The results are compared to those reported previously from phenyl phenylacetate and 1-naphthyl tetradecanoate to assess the influence of a long alkyl chain on the in-cage motions of the intermediate singlet radical pairs. It is demonstrated that the reactivity and selectivity of intimate singlet radical pairs can be tuned by judicious placement of long-chain substituents and selection of a specific polyethylene type as the reaction matrix.

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Section: Resultsmentioning

confidence: 88%

“…Dodecylphenol (POL) was obtained during synthesis of DPPA (see SUPPLEMENTAL MATERIALS): mp 64.5-65.7"C (lit [36]. mp 65.5-66°C); mass m/z calculated for CI8H3"0 262, found 262.…”

mentioning

confidence: 99%

Comparisons of Photo-Fries Rearrangements of 4-Dodecylphenyl Phenylacetate and Two Structurally Related Esters in Hexane and Polyethylene Cages. How Important Are Anchoring Chains?†

Luo

Passin

Weiss

2006

Photochem Photobiol

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The F ries Reaction

Blatt

2011

Organic Reactions

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The Fries reaction consists in the conversion of an ester of a phenol to an ortho‐ or para‐hydroxyketone, or a mixture of both, by treatment with aluminum chloride. Three different mechanisms for the fries rearrangement have received serious consideration.: the ester is assumed to react with aluminum chloride to give an acid chloride and a phenoxyaluminum chloride which combine to form a derivative of the hydroxyketone; one molecule of the phenyl ester is acylated by another molecule; the Fries reaction is considered ti be a true intramolecular rearrangement in which the acyl group shifts directly from the oxygen atom to the carbon atom of the ring.

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