
%0 Journal Article
%A Eichholzer, JV 
%A Macleod, JK 
%A Summons, RE 
%T Studies of the thermal N 3 to N 9 rearrangement of the 3-&#946;-D-Glucoside of the cytokinin, 6-benzylaminopurine
%J Australian Journal of Chemistry
%D 1978/04/01
%V 31
%N 4
%P 893-899
%K 
%R https://doi.org/10.1071/CH9780893
%U https://www.publish.csiro.au/paper/CH9780893 
%X 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. 
