119205-35-5Relevant articles and documents
Aromatic substituent effects in the breakdown of methyl hemiacetals of α-bromoacetophenone
Soerensen, Poul E.,Loegager, Tine,Kanagasabapathy, V. M.,McClelland, Robert, A.
, p. 313 - 316 (2007/10/02)
Rate constants for H+, OH-, acetate and water catalysis of the breakdown of three methyl hemiacetals of α-bromoacetophenone (4-MeO, 4-Cl and unsubstituted) have been measured.These hemiacetals are generated by aqueous bromination of the appropriate α-methoxystyrene.The rate constants correlate with the Hammet ? constnat with ρ values of -2.2 (H+), -0.4 (OH-), +0.6 (H2O) and +0.1 (acetate).These values are, within experimental error, the same as those reported previously for hemiacetals of benzaldehyde.This leads to the conclusion that the ketone derivatives undergo breakdown by the same catalyzed mechanism as the aldehyde derivatives.