Chemistry of N-haloamines. XXII. Rearrangement of o-hydroxyaldehydes and ketones to o-hydroxyanilides by monochloroamine

Crochet, Roy A.; Sullivan, F. Ryan; Kovacic, Peter

doi:10.1021/jo00935a007

Cited by 4 publications

(1 citation statement)

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“…o-Hydroxyacetophenone was found to oxidize about 180 times faster than the p-isomer (Table 5), ~h i c h required decreasing the reaction temperature to 0°C to allow the same kinetic methods to be used. Similarly faster ortho than para ketone oxidation has been observed for chloran~ine oxidation of hydroxyacetophenones (42), and for the Baeyer-Villiger oxidation of nitroacetophenones (24).…”

Section: Resultsmentioning

confidence: 53%

Kinetic studies of Dakin oxidation of o- and p-hydroxyacetophenones

Hocking¹,

Ong²

1977

Can. J. Chem.

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Rates of oxidation of aqueous o-, and p-hydroxyacetophenone with alkaline hydrogen peroxide to yield catechol and hydroquinone, respectively, have been followed spectrophotometri-cally. Both ketones showed smooth pseudo first-order behaviour, the ortho isomer yielding rate constants in the range 2.6 to 6.6 × 10−2 min−1 at 0 °C, and the para isomer of 0.73 to 7.10 × 10−2 min−1 at 35 °C for the concentrations of hydrogen peroxide and base used. The order in hydrogen peroxide was, unexpectedly, found to be 1.4. A simple test established that this fractional order was probably not the result of hydrogen peroxide involvement in simultaneous first- and second-order processes of differing rates. Other plausible pathways to explain this are proposed.

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Section: Resultsmentioning

confidence: 53%