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

Research output: Contribution to journalArticle

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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dioxane
erythritol
kinetics
spectroscopy
nitrobenzoic acids

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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.
Awal, Abdul ; Boyd, A. S F ; Grant Buchanan, J. ; Edgar, Alan R. / The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control. In: Carbohydrate Research. 1990 ; Vol. 205, No. C. pp. 173-179.
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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. {\circledC} 1990.",
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Awal, A, Boyd, ASF, Grant Buchanan, J & Edgar, AR 1990, 'The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control', Carbohydrate Research, vol. 205, no. C, pp. 173-179.

The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control. / Awal, Abdul; Boyd, A. S F; Grant Buchanan, J.; Edgar, Alan R.

In: Carbohydrate Research, Vol. 205, No. C, 19.09.1990, p. 173-179.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control

AU - Awal, Abdul

AU - Boyd, A. S F

AU - Grant Buchanan, J.

AU - Edgar, Alan R.

PY - 1990/9/19

Y1 - 1990/9/19

N2 - 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.

AB - 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.

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