A new synthesis of o-di-t-butylbenzene and t-butylmesitylene

Finnegan, R.A.; Knutson, D.

doi:10.1039/c19660000172

Cited by 8 publications

(10 citation statements)

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“…Finnegan and Knutson detected decarbonylation of the acyl fragment when highly hindered aryl carboxylates were irradiated. 8,9 Barton and coworkers19 found that irradiation of ßnaphthyl fluorene-9-carboxylate gave high yields of carbon monoxide and /3-naphthol, apparently via decarbonylation of the 9-acylfluorene radical to give the stabilized 9-fluorenyl radical. In a somewhat (18) W. M. Horspool and P. L. Parson, J. Chem.…”

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confidence: 99%

Mechanistic studies of the photo-Fries reaction

Sandner¹,

Hedaya²,

Trecker³

1968

J. Am. Chem. Soc.

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Detailed product analyses and quantum yield determinations were carried out on the 2537-A lightinduced reactions of p-tolyl acetate, benzoate, and hydrocinnamate. Evidence is presented that the photo-Fries rearrangement originates from an upper singlet state and proceeds to product by a molecular pathway that is independent of its reaction environment. A 1,3-sigmatropic shift is proposed. p-Cresol formation, on the other hand, was shown to be highly solvent dependent and appears to arise from reactions of the p-methylphenoxy radical. Studies with p-tolyl acetate-d3 showed that alcoholic solvent derived esters, which are formed as coproducts, originate, at least in part, from a ketene intermediate. A comprehensive scheme involving a multiplicity of reaction paths is proposed to account for these results.hotochemical analogs of the Fries2v3 and Claisen4 P rearrangements have received considerable attention in recent years, as have photoinduced rearrangements of

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confidence: 99%

Mechanistic studies of the photo-Fries reaction

Sandner¹,

Hedaya²,

Trecker³

1968

J. Am. Chem. Soc.

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“…Four of the five minor photoproducts result from the reactions of methyl and phenoxy radicals, oand p-cresols and o-and p-hydroxydiphenyl ethers result in Scheme IV either from radical-radical coupling reactions of methyl or phenoxy radical and another phenoxy radical (8)(9)(10)(11) or by means of radical attack on a phenyl acetate molecule (12)(13)(14)(15). These reactions result in the formation of substituted cyclohexadien ones which would be expected to enolize rapidly under the conditions of the experiments to give the substituted phenols (16)(17)(18)(19).…”

Section: Discussionmentioning

confidence: 99%

Mechanism of photochemical reactions in solution. LXX. Photolysis of aryl esters

Meyer¹,

Hammond²

1972

J. Am. Chem. Soc.

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“…A further side reaction, occurring especially upon photolysis of phenyl esters with a high steric barrier, is decarboxylation. Though exact facts influencing the relation between rearrangement and decarboxylation are not known, it is obvious that photodecarboxylation can be useful for the preparation of certain biaryls and alkylaryls (33). Thus 2,4,6-tri-¿-butylbiphenyl (XVII) can be prepared according to Eq 4; o-di-f-butylbenzene from o-f-butylphenyl pivalate (33), p-cresylferrocene from p-cresyl ferrocenoate (34) fete.…”

Section: Mono and Diaryl Estersmentioning

confidence: 99%

“…Though exact facts influencing the relation between rearrangement and decarboxylation are not known, it is obvious that photodecarboxylation can be useful for the preparation of certain biaryls and alkylaryls (33). Thus 2,4,6-tri-¿-butylbiphenyl (XVII) can be prepared according to Eq 4; o-di-f-butylbenzene from o-f-butylphenyl pivalate (33), p-cresylferrocene from p-cresyl ferrocenoate (34) fete. The last side reaction observed in the photolysis of phenyl esters is the formation of a carboxylic acid corresponding to the initial ester (Eq 5) (34,49,79).…”

Section: Mono and Diaryl Estersmentioning

confidence: 99%