H. Burrows, R. M. Topping
1970
Citations
0
Influential Citations
2
Citations
Journal
Journal of The Chemical Society B: Physical Organic
Abstract
Under comparable conditions in aqueous ethanol the hindered ester, 2-acetylphenyl mesitoate (IV) was hydrolysed 130 times more rapidly than the 4-isomer (V) as a result of participation by the keto-carbonyl group. Such participation in anhydrous methanol was shown to result in the formation of the dimethyl acetal (IX) of 2-hydroxy-acetophenone under basic conditions and to support a mechanism involving intramolecular nucleophilic attack by the conjugate base of the solvated keto-carbonyl group upon the ester carbonyl group of the ester (IV). That this attack is, in part, rate determining, was shown by the much greater susceptibility to intramolecular cyclisation of the unhindered ester, 2-acetylphenyl benzoate (X).