Preparative flash vacuum thermolysis. Homolytic cleavage of isomannide and isosorbide dinitrate to 1,4,3,6-dianhydrohexoses
1987
1,4,3,6-dianhydromannopyranose (3) can be conveniently prepared by flash vacuum thermolysis of isomannide dinitrate (1), while its epimer isosorbide dinitrate (2) yields a mixture of (3) and 1,4,3,6-dianhydrofructose (5), reflecting the restricted number of rearrangements, in one case with inversion of configuration, possible in the intermediate cis-fused furofuran radicals.
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