
TY  - JOUR
A1  - Eichholzer, JV 
A1  - Macleod, JK 
A1  - Summons, RE 
T1  - Studies of the thermal N 3 to N 9 rearrangement of the 3-&#946;-D-Glucoside of the cytokinin, 6-benzylaminopurine
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 4
SP  - 893
EP  - 899
KW  - 
UR  - https://doi.org/10.1071/CH9780893 
N2  - The initial observation of a rearrangement of the glucosyl residue from N 3 to N 9 during g.c.-m.s. of derivatives of the 3-&#946;-D-glucosyl metabolite of 6-benzylaminopurine (1) has been further investigated by g.c., g.c.-m.s. and p.m.r. of the permethylated and perdeuteromethylated derivatives of (1). Results show that the major process is a thermal intramolecular 1,3-shift of the glucosyl grouping to the 9-position with retention of configuration at the migrating centre, together with a smaller contribution from an intermolecular 1,3-rearrangement which gives rise to both the 9-&#945;- and 9-&#946;-anomers. An ionic mechanism is proposed to explain both rearrangement processes. 
ER  -

