Allylic nucleophilic substitution reactions in sugars. III. Uncatalysed displacements in hexamethylphosphoramide
- 1 January 1980
- journal article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 33 (11) , 2499-2508
- https://doi.org/10.1071/ch9802499
Abstract
The uncatalysed displacement of allylic benzoyloxy groups with azide in unsaturated sugars has been studied by using hexamethylphosphoramide as solvent. Tri-O-benzoylglycals and 4,6-O-benzylidene-3-O-benzoylglycals were investigated. The former gave rise to mixtures of 3-azido-glycals and hex-2-enopyranosyl azides, whereas the latter gave only glycal products. The mechanism of the reactions is considered in some detail. Displacements on allylic trimethylsilyl ethers were not successful.Keywords
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