Please use this identifier to cite or link to this item:
https://doi.org/10.1039/C39910000690
Title: | Free radical substitutions of acyloxy groups in carbohydrate α-ketoesters |
Authors: | Ferrier, R.J. Lee, C.-K. Wood, T.A. |
Issue Date: | 1991 |
Source: | Ferrier, R.J., Lee, C.-K., Wood, T.A. (1991). Free radical substitutions of acyloxy groups in carbohydrate α-ketoesters. Journal of the Chemical Society, Chemical Communications (10) : 690-691. ScholarBank@NUS Repository. https://doi.org/10.1039/C39910000690 |
Abstract: | A range of carbohydrate derivatives containing α-ketoester functionality undergo efficient reductive loss of the acyloxy groups when treated with tri-n-butyltin hydride in refluxing benzene and in the presence of azoisobutyronitrile (AIBN) as radical initiator; under similar conditions, but with allyltri-n-butyltin instead of the hydride, efficient α-C-allylation takes place with axial substitution occurring preferentially in compounds with the ketoesters located within conformationally stable pyranoid rings; the methods represent novel ways of deoxygenating carbohydrate derivatives and of introducing branch points. |
Source Title: | Journal of the Chemical Society, Chemical Communications |
URI: | http://scholarbank.nus.edu.sg/handle/10635/76223 |
ISSN: | 00224936 |
DOI: | 10.1039/C39910000690 |
Appears in Collections: | Staff Publications |
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