40231-09-2Relevant academic research and scientific papers
Kinetics and mechanism of the intramolecular substitution of acetate in 2′-hydroxyphenacyl acetate: 2′-hydroxyphenacyl as a potential protective group for carboxylic acids
Ogle, Colin R.,Main, Lyndsay
, p. 472 - 473 (2007/10/03)
2-Acetoxy-2′-hydroxyacetophenone (1c) undergoes cyclisation in water via its phenolate ion to release acetate and coumaran-3-one (2) at rates defined by the equation kobs = k1/[1+(10-pH)/Ka] where k1, the first order rate coefficient for the cyclisation of the phenolate ion, is 8.6 × 10-4 s-1 and Ka, the ionisation constant for 2′-OH is 2.0 × 10-9 (pKa 8.70) at 30°C.
Photolysis of Enol Acetates and α-Bromo Derivatives of o-(Acyloxy)acetophenones
Garcia, Hermenegildo,Martinez-Utrilla, Roberto,Miranda, Miguel A.
, p. 589 - 598 (2007/10/02)
UV irradiation of enol acetates 3a-g in benzene gives mainly o-(acetoxy)acetophenones 2 and 2-methylchromones 4. Under the same conditions, the dimethyl derivatives 3h and 3i remain unaffected.The α-bromo ketone 5a gives rise to mixtures of o-(acetoxy)acetophenone (2a), the diketone 6, and/or α-acetoxy-o-hydroxyacetophenone (7), depending on the irradiation conditions.The similarities and differences between the two series of experiments, as well as their possible mechanistic implications, are discussed.
