23261-21-4Relevant academic research and scientific papers
The Base-Catalysed Rearrangement of Dibromo Alditols via Epoxide Migration
Bock, Klaus,Castilla, Ines Maya,Lundt, Inge,Pedersen, Christian
, p. 264 - 268 (2007/10/02)
The reaction of 2,6-dibromo-2,6-dideoxy-D-mannitol (1) and -D-glucitol (12) with aqueous base has been studied.With potassium carbonate 1 forms epoxides which are subsequently hydrolysed to a mixture of D-mannitol and D-glucitol.The same treatment of 12 yields almost only D-glucitol.With aqueous potassium hydroxide both 1 and 12 undergo rearrangement through epoxide migration.Thus 1 is mainly converted into 2,5:3,4-dianhydro-L-altritol (10) whereas 12 yields 1,4:3,6-dianhydro-L-glucitol (18).The reactions were monitored using 13C NMR spectroscopy.
