
TY  - JOUR
A1  - Guthrie, RD 
A1  - Irvine, RW 
A1  - Jenkins, ID 
T1  - Allylic nucleophilic substitution reactions in sugars. III. Uncatalysed displacements in hexamethylphosphoramide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 11
SP  - 2499
EP  - 2508
KW  - 
UR  - https://doi.org/10.1071/CH9802499 
N2  - 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. 
ER  -

