Abstract
The acyl group migration in partially acylated glycerides are initiated and directed by ion pairs which are formed by the action of acid, base or heat upon glycerides under anhydrous conditions. This ion pair can also be created specifically by reaction of sodium 1,2-isopropylideneglyceroxide with glycerideiodides. The elimination of sodium iodide results in 1,2-isopropylideneglyceryl-glyceride ion pair. In such an ion pair the acyl groups follow both migration mechanisms intermolecular and intramolecular whereas, in a glyceride-glyceride ion pair it seems that only an intermolecular exchange of acyl groups takes place. The free hydroxyl group and hydroxyl hydrogen atom in carbonium ion (Experiment 3, fig. 3, mb) are also subjected to the rearrangement within the ion pair. The rearrangement of hydroxyl group and hydroxyl hydrogen atom has certain connection with the acyl group migration within the same ion pair. The above evidence is based on experiments which are reported.
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