Peter Norris , Department of Chemistry, Youngstown State University, Youngstown, OH

1. Stereospecific Intramolecular Carbenoid Insertions on Furanose Platforms as a Route to Branched-chain Sugars, C-Glycosides, and Fused Heterocycles Peter Norris, Department of Chemistry, Youngstown State University, Youngstown, OH • One-pot Azidation: Arylsulfonyl azides, which are classically used for diazo-transfer chemistry, have been shown now to be useful in one-pot transformations of alcohols into alkyl azides. Use of NaH and either p-ABSA or p-NBSA results in the conversion of primary alcohols, including those of protected carbohydrates, to the azide in high yield. Secondary alcohols react more slowly and also result in side-products such as SNAr and oxidation outcomes. • Green Azidation Chemistry: The isolation of unexpected azido-deoxy sugar derivatives during our study of diazo-transfer/decomposition chemistry on furanoses has lead to several convenient one-pot approaches to azide synthesis. We are now able to generate an organic-soluble azide salt efficiently in ethanol solution that subsequently reacts with alkyl and acyl halides efficiently. The azide products, which are not isolated, then serve as substrates for additional reactions such as 1,2,3-triazole synthesis.