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- Title
Chemistry of Organo Halogenic Molecules. Part 229. The Role of Iodine in Acetyl Group Transfer to Oxygen-containing Molecules under Solvent-free Reaction Conditions.
- Authors
Jereb, Marjan; Vražič, Dejan; Zupan, Marko
- 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.
- Subjects
IODINE; ALDEHYDES; ORGANOHALOGEN compounds; CHEMICAL reactions; REACTIVITY (Chemistry); ESTERIFICATION
- Publication
Acta Chimica Slovenica, 2009, Vol 56, Issue 3, p652
- ISSN
1318-0207
- Publication type
Article