73589-85-2Relevant articles and documents
Kinetics and Mechanism of Acid-catalysed Addition of Methanol to α-Methoxystyrenes
Toullec, Jean,El-Alaoui, Mohiedine,Bertrand, Roland
, p. 1517 - 1522 (2007/10/02)
A kinetic study of the complex behaviour of ring-substituted α-methoxystyrenes in acidic (HBr) methanol is reported.The reaction yields the corresponding acetals as the only kinetic products; these are subsequently partly hydrolysed into acetophenones with rates only a little lower than those of their formation.The rate-limiting step for methanol addition corresponds to proton attachement to the double bond, yielding an oxocarbenium ion which is trapped by methanol with a rate constant 10E4 higher than that of ion deprotonation.The rate constants for proton transfer from CH3OH2+ are in the same range of magnitude as those for proton transfer from H3O+ in water.The lyonium ion catalytic constants fit a good Young-Jencks equation with ρn-2.86 and ρr-1.28