The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control

Abdul Awal, A. S F Boyd, J. Grant Buchanan, Alan R. Edgar

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Abstract

The isopropylidenation of erythritol, under conditions of kinetic control, employing 2-methoxypropene, yielded the 1,2:3,4- (1, 50%), the 1,4:2,3- (2, 18%), and the novel 1,3:2,4-diacetal (3, 5%). Under similar conditions, ribitol gave the known 1,2:4,5- (4, 36%) and 1,4:2,3-diacetal (7, 3%) together with the new 1,3:4,5- (8, 12%) and 1,3:2,5- diacetal (11, 5%), a further example of a dioxepane ring. 13C-N.m.r. and 1H-n.m.r. spectroscopy showed that the 1,3-dioxane rings in 3, 8, and 11 adopt chair conformations. In 9, the p-nitrobenzoate of 8, the dioxane chair is flattened. The product composition is compared with that from the equilibrated system. © 1990.

Original languageEnglish
Pages (from-to)173-179
Number of pages7
JournalCarbohydrate Research
Volume205
Issue numberC
Publication statusPublished - 19 Sep 1990

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    Awal, A., Boyd, A. S. F., Grant Buchanan, J., & Edgar, A. R. (1990). The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control. Carbohydrate Research, 205(C), 173-179.