Journal of Organic Chemistry p. 2106 - 2111 (1995)
Update date:2022-08-11
Topics:
Tanaka, Mutsuo
Fujiwara, Masahiro
Ando, Hisanori
The influence of the protonation on Gattermann-Koch formylation rate of alkylbenzenes was studied in CF3SO3H-SbF5.From the kinetic study of m-xylene formylation using various SbF5:m-xylene molar ratios in CF3SO3H, it is revealed that the formylation rate is explained with the equations which take into account the protonation equilibrium of m-xylene, and the apparent formylation rate is decreased by the protonation.The decrease of the apparent formylation rate by the protonation is proportional to the ratio of protonated alkylbenzene to form the ?-complex; therefore, the apparent relative formylation rate of alkylbenzenes is not consistent with their relative basicity under strong acidic conditions such as in CF3SO3H-SbF5.
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