Photolysis of acetylated 1-cyano-D-glycopyranosyl azides led to the corresponding acetylated 4,5,6,7-tetrahydro-1,3-oxazepines, being isolated in moderate to good yields (34-58%). These ring-expanded compounds were formed by rearrangements involving migration of the endocyclic carbon atom attached to the anomeric centre. This seems to be the preferred reaction pathway, whatever the anomeric configuration (α/β) of the acetylated 1-cyano-D-glycopyranosyl azide used as the substrate. Rearrangement occurred without changing the stereochemistry of the migrating carbon. Photo-rearrangement of D-glycopyranosyl azides having either a carboxamido- or a tetrazolyl-anomeric group gave complex reaction mixtures. Copyright (C) 2000 Elsevier Science Ltd.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry