
%0 Journal Article
%A Guthrie, RD 
%A Irvine, RW 
%A Jenkins, ID 
%T Allylic nucleophilic substitution reactions in sugars. III. Uncatalysed displacements in hexamethylphosphoramide
%J Australian Journal of Chemistry
%D 1980/11/01
%V 33
%N 11
%P 2499-2508
%K 
%R https://doi.org/10.1071/CH9802499
%U https://www.publish.csiro.au/paper/CH9802499 
%X 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. 
