Abstract
Carbohydrate free radicals wer regiospecifically generated at C-1 of acylated and alkylated pyranosyl derivatives in non-aqueous solution and their conformations were deduced from the hyperfine splittings of their e.s.r. spectra. The preferred conformations of the pyranosyl radicals are discussed in terms of a stabilizing interaction of the singly occupied p-orbital with the σ*-LUMO of the adjacent β-C–OR bond. From the α-13C coupling constant of the tetra-acetylglucosyl radical it is concluded that pyranosyl radicals are of π-type.
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