Marjan Jereb,1,* Dejan Vražič2 and Marko Zupan1
1 Faculty of Chemistry and Chemical Technology, University of Ljubljana,
Aškerčeva 5, 1000 Ljubljana, Slovenia
2 Present address: Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia
* Corresponding author: E-mail: marjan.jereb@fkkt.uni-lj.si
Abstract
Iodine was shown to be an efficient catalyst for the conversion of
phenyl-substituted aldehydes to the corresponding
1,1-diacetate derivatives under solvent-free reaction conditions (SFRC), which
are superior to the classical solution conditions.
It was demonstrated that the order of the addition of reactants was of
fundamental importance; the ability of
substituents on the phenyl ring modified reactivity irrespectively to electronic
properties, the pentafluorophenyl group
significantly reduced reactivity of the aldehyde. Alcohols yielded acetates;
acetic anhydride was found to be the most efficient
reagent; isopropenyl acetate and vinyl acetate were less reactive; however the
pentafluorophenyl group enhanced
reactivity with the latter two reagents. Beside the esterification of benzyl
alcohol and its pentafluorophenyl analogue,
the formation of acetals was also observed.
Keywords: Iodine, catalyst, solvent-free, acetylation.