REACTIVITY CONTROLLED BY LATTICE INTERACTIONS IN CRYSTAL - INTERMOLECULAR ACYL TRANSFER IN (+ -)-2,4-DI-O-BENZOYL-MYO-INOSITOL 1,3,5-ORTHOFORMATE/

(+/-)-2,4-Di-O-benzoyl-myo-inositol 1,3,5-orthoformate, on heating in the presence of a base, undergoes transesterification to give 2,4,6-tr i-O-benzoyl-myo-inositol 1,3,5-orthoformate and 2-O-benzoyl-myo-inosit ol 1,3,5-orthoformate in the solid state. The same reaction can also b e performed by microwave irradiation instead of heating. The crystal s tructure of the dibenzoate reveals that the screw-axis-related molecul es have the hydroxyl and the carbonyl groups ideally oriented for the reaction and gives a close picture of how such a reaction proceeds in enzymes. The structure of the corresponding acetate, (+/-)-2-O-benzoyl -4-O-acetyl-myo-inositol 1,3,5-orthoformate, lacks this geometry and h ence is unreactive in the solid state. Both the acetate and the benzoa te undergo base-catalyzed transesterification in solution.